Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester
CAS No.:345342-63-4
Molecular Formula:C₂₉H₃₂O₉S
Molecular Weight:556.634
Hs Code.:

Synonyms:Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester 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: 94.0%

: 124-63-0
methanesulfonyl chloride

: 345342-54-3
Benzoic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-5-methyl-tetrahydro-pyran-3-yl ester

: 345342-63-4
Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

: 79549-73-8
benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

: 345342-63-4
Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

2.1: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: 66 percent / diethyl ether / 0.5 h / -78 °C

5.1: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

6.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

6.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

7.1: 94 percent / N-ethyl-diisopropylamine / CH₂Cl₂ / 0.5 h

With hydrogenchloride; 3 A molecular sieve; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol010089t

Reference yield:

: 345342-71-4
(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 345342-63-4
Benzoic acid (2S,3R,4R,5R,6R)-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-4-methanesulfonyloxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

2.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

3.1: 66 percent / diethyl ether / 0.5 h / -78 °C

4.1: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

5.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

5.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

6.1: 94 percent / N-ethyl-diisopropylamine / CH₂Cl₂ / 0.5 h

With hydrogenchloride; 3 A molecular sieve; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1021/ol010089t