(1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

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Chemical Name:(1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol
CAS No.:685835-97-6
Molecular Formula:C₂₁H₂₆O₄S
Molecular Weight:374.501
Hs Code.:

Synonyms:(1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

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Chemical Property of (1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

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Technology Process of (1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

There total 6 articles about (1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

: 100-39-0
benzyl bromide

: 685835-96-5
(1R)-2-O-isopropanesulfonyl-1-O-(Z-prop-1'-en-1'-yl)-1-phenyl-1,2-ethanediol

: 685835-97-6
(1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

Guidance literature:: (1R)-2-O-isopropanesulfonyl-1-O-(Z-prop-1'-en-1'-yl)-1-phenyl-1,2-ethanediol; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; at -78 ℃;

benzyl bromide; In tetrahydrofuran; at -20 ℃; for 1h;
DOI:10.1016/j.bmc.2003.10.043

Reference yield:

: 16355-00-3
(R)-1-phenyl-1,2-ethanediol

: 685835-97-6
(1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / CH₂Cl₂ / 3 h

2.1: 96 percent / NaH / dimethylformamide; various solvent(s) / 2 h / 20 °C

3.1: 96 percent / p-TsOH / methanol / 1 h

4.1: 89 percent / t-BuOK / dimethylsulfoxide / 1.5 h / 55 °C

5.1: 94 percent / Et₃N / CH₂Cl₂ / 13 h / 10 °C

6.1: DMPU; n-BuLi / tetrahydrofuran / -78 °C

6.2: 58 percent / tetrahydrofuran / 1 h / -20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2003.10.043

Reference yield:

: 80595-15-9
(1R)-1-phenyl-2-O-triphenylmethyl-1,2-ethanediol

: 685835-97-6
(1R)-2-O-(1'',1''-dimethyl-2''-phenyl-ethanesulfonyl)-1-phenyl-1-O-(Z-prop-1'-en-1'-yl)-1,2-ethanediol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / NaH / dimethylformamide; various solvent(s) / 2 h / 20 °C

2.1: 96 percent / p-TsOH / methanol / 1 h

3.1: 89 percent / t-BuOK / dimethylsulfoxide / 1.5 h / 55 °C

4.1: 94 percent / Et₃N / CH₂Cl₂ / 13 h / 10 °C

5.1: DMPU; n-BuLi / tetrahydrofuran / -78 °C

5.2: 58 percent / tetrahydrofuran / 1 h / -20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2003.10.043