IDNameStructure

NA

Deuterated carboxylic acids

D 3C

Reference

CO2H

DD
DS-YS001

Y. Sawama, H. Sajiki et al., Adv. Synth. Catal. 2016, 358,

n3277. https://doi.org/10.1002/adsc.201600363

D DD D

heptanedioic-d10 acid

HO2C

Y. Sawama, H. Sajiki et al., Adv. Synth. Catal. 2016, 358,

CO2H

D DD D D D
DS-YS002

2-(propyl-d7)pentanoic2,3,3,4,4,5,5,5-d8 acid(valproic acid-d8)

NA

D DD
D3C

D DD DD(2R,3S,4S,5R,6R)-2(hydroxymethyl-d2)-6methoxytetrahydro-2H-pyran3,4,5-d3-3,4,5-triolDS-YS004(hydroxymethyl-d2)-5-2303.

Y. Sawama, H. Sajiki et al., Adv. Synth. Catal. 2018, 360, 230.

CO2R

https://doi.org/10.1002/adsc.201800170

D D OH
DDO
HOOMeHOOH
D(2R,3S,4R,5R)-2-HO

https://doi.org/10.1002/adsc.201600363

https://doi.org/10.1002/adsc.201800170

DDS-YS003

3277.

Y. Sawama, H. Sajiki et al., Adv. Synth. Catal. 2018, 360,

CD3

Deuterated methacrylatemonomers

CD3

CO2R

D

https://doi.org/10.1002/adsc.201600363
Y. Sawama, H. Sajiki et al., Adv. Synth. Catal. 2016, 358,DDeuterated acrylate monomers

DNACO2H
D D3277.

DDY. Sawama, H. Sajiki et al., Chem. Eur. J., 2013, 19, 484.
https://doi.org/10.1002/chem.201203337

Y. Sawama, H. Sajiki et al., Chem. Eur. J., 2013, 19, 484.

D O D OMe

https://doi.org/10.1002/chem.201203337

methoxytetrahydrofuran-3,4-d2-HO

3,4-diol
DS-YS005

D
D
DS-YS006

DNANA

Deuterated alkanes

DDDDn DDDD

Deuterated alkynes

Deuterated aldehydes

DD

DDY. Sawama, H. Sajiki et al., Org. Process Res. Dev. 2019, 23,

D648. https://doi.org/10.1021/acs.oprd.8b00383

OOH DDFNAO

Dbis(4-fluorophenyl-2,3,5,6d4)methanolDD

2H-chromen-2-one-d6OH

D

Y. Sawama, H. Sajiki et al., Org. Process Res. Dev. 2019, 23,

D648. https://doi.org/10.1021/acs.oprd.8b00383

F
Y. Sawama, H. Sajiki et al., RSC Adv. 2015, 5, 13727.
https://doi.org/10.1039/C4RA16386A

Y. Sawama, H. Sajiki et al., RSC Adv. 2015, 5, 92954

R

https://doi.org/10.1039/C5RA18921G

Ar CDO

Y. Sawama, H. Sajiki et al., Synlett 2020, 31, 699.
https://doi.org/10.1055/s-0040-1707993

DS-YS007

D D CD3C

PBnMMA-d5

ODS-Y. Sawama, H. Sajiki et al., Adv. Synth. Catal. 2018, 360,OBn

https://doi.org/10.1002/adsc.201800170

2-amino-9-((2R,5R)-3,4-d2)tetrahydrofuran-2-yl-3,4-d2)1,9-dihydro-6H-purin-6-one

NHODD

N
D O (D)

D D

propan-1,1,2,2-d4-1-ol-dNH
N

https://doi.org/10.1039/D2SC90156K

D D 97% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OD
D D10% DDS-HN003

4-(1-cyclohexyl-1H-tetrazol-5yl)butan-1,1,2,2-d4-1-ol

DS-HN004

N NN

https://doi.org/10.1039/D2SC90156K

97% D D DN4OH

D D
65% D

pentane-1,1,5,5-d4-1,5-diol-d2

91% D
D D

D D
DO
DS-HN005

DS-HN006

96% D
OH

D D

o-tolylmethan-d2-ol

DS-HN008

DS-HN009

96% DOH

D D

p-tolylmethan-d2-ol

95% DOH

D D(4-fluorophenyl)methan-d2-ol

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

https://doi.org/10.1039/D2SC90156K

D D

m-tolylmethan-d2-ol

https://doi.org/10.1039/D2SC90156K

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

93% D

OH

DS-HN007

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OD

D D

phenylmethan-d2-ol

NH2Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

97% DOD
D D
13% D
butan-1,1,2,2-d4-1-ol-d

https://doi.org/10.1002/chem.201203337(OH)

HODS-HN002

Y. Sawama, H. Sajiki et al., Chem. Eur. J., 2013, 19, 484.

O

dihydroxy-5-(hydroxymethyl-DS-HN0012303.

nNaka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

95% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OH

https://doi.org/10.1039/D2SC90156K

FDS-HN010

D D(4-bromophenyl)methan-d2-ol

Br

95% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OH

https://doi.org/10.1039/D2SC90156K

DS-HN011

D D(4(trifluoromethyl)phenyl)methand2-ol

DS-HN012

96% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OH

https://doi.org/10.1039/D2SC90156K

F3C

D D
96% D
OH

(4-nitrophenyl)methan-d2-ol

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

O2 N
DS-HN013

pyridin-2-ylmethan-d2-ol

N

DS-HN014

butan-2-d-2-ol-d

D D

96% DOHDO D 86% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

DS-HN015

cyclohexan-1-d-1-ol-dD
DS-HN016

DS-HN017

DS-HN018

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OD
91% D

HO D

1-phenylethan-1,2,2,2-d4-1-ol

63% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

CD3
65% D

https://doi.org/10.1039/D2SC90156K

HO D

1-(p-tolyl)ethan-1-d-1-ol

97% DCH3HO D

1-(4-bromophenyl)ethan-1-d-1-

https://doi.org/10.1039/D2SC90156K

97% D
CH3ol

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

BrDS-HN019

HO D

cyclopropyl(phenyl)methan-d-96% D

https://doi.org/10.1039/D2SC90156K

ol

DS-HN020

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

HO D 94% D

diphenylmethan-d-ol

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

DS-HN021

96% D
Cl D D

Rapidosept-d2(2,4-dichlorophenyl)methan-d2-Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

OHolClDS-HN022

Tyrosol-d4

94% D
D D

4-(2-hydroxyethyl-1,1,2,2d4)phenol

HONaka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OH

D D
95% D

https://doi.org/10.1039/D2SC90156K

DS-HN023

95% D
D OHOOH

Guaifenesin-d3
3-(2-12Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.
https://doi.org/10.1039/D2SC90156K

26 D D
OCH3 94% D

methoxyphenoxy)propane1,1,2-d3-1,2-diol
DS-HN024

Diprophylline-d5

98% D

7-(2,3-dihydroxypropyl1,1,2,3,3-d5)-1,3-dimethyl-3,7-O
H3 C

dihydro-1H-purine-2,6-dione

DNNN

NO

DD

D 96% D

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

OH

https://doi.org/10.1039/D2SC90156K

OH
D 96% D67

CH3DS-HN025(4-(ethynyl-d)phenyl)methanol

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

H H <3% D

https://doi.org/10.1039/D2SC90156K

HO

97% D
DDS-HN026

1-phenylprop-2-yn-3-d-1-ol

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

<3% DH OH

https://doi.org/10.1039/D2SC90156K

D
94% D
DS-HN027

Losartan potassium-d2N N

5-(4'-((2-butyl-4-chloro-5(hydroxymethyl-d2)-1Himidazol-1-yl)methyl)-[1,1'biphenyl]-2-yl)tetrazol-2-ide

NKN

Naka, H. et al., Chem. Sci. 2022, 13, 8744–8751.

96% D DDOHNClN

https://doi.org/10.1039/D2SC90156K