1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

Base Information

Chemical Name:1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate
CAS No.:136089-06-0
Molecular Formula:C₃₈H₄₀O₇S
Molecular Weight:641.789
Hs Code.:

Synonyms:1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

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Chemical Property of 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

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Technology Process of 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

There total 6 articles about 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate 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: 82.0%

: 136089-04-8
(1R,2R)-1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1-deuteriopropane-2,3-diol

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 136089-06-0
1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

Guidance literature:: In benzene; at 70 ℃; for 12h;
DOI:10.1021/jo00022a038

Reference yield:

: 113019-43-5
2,6-Anhydro-3,4,5,7-tetra-O-benzyl-aldehydo-D-glycero-D-ido-heptopyranose

: 136089-06-0
1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

Guidance literature:: Multi-step reaction with 4 steps

1: benzene / Ambient temperature

2: 89 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / 0 °C

3: 1.) BD₃, 2.) 10percent aq. NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 7 h, 2.) 0 deg C, 1 h

4: 82 percent / benzene / 12 h / 70 °C

With sodium hydroxide; dihydrogen peroxide; borane-d3; diisobutylaluminium hydride; In hexane; dichloromethane; benzene;
DOI:10.1021/jo00022a038

Reference yield:

: 79258-16-5
2,6-anhydro-1,3,4,5-tetra-O-benzyl-D-glycero-L-gulo-heptitol

: 136089-06-0
1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-1(R)-deuteriopropane-2,3-(2R)-diol 2,3-thionocarbonate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 40 min, 2.) 0 deg C, 10 min

2: benzene / Ambient temperature

3: 89 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / 0 °C

4: 1.) BD₃, 2.) 10percent aq. NaOH, 30percent H₂O₂ / 1.) THF, room temperature, 7 h, 2.) 0 deg C, 1 h

5: 82 percent / benzene / 12 h / 70 °C

With sodium hydroxide; oxalyl dichloride; dihydrogen peroxide; borane-d3; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; benzene;
DOI:10.1021/jo00022a038