(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

Base Information

Chemical Name:(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol
CAS No.:345342-62-3
Molecular Formula:C₂₁H₂₆O₆
Molecular Weight:374.434
Hs Code.:

Synonyms:(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol 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: 100.0%

: 345342-56-5
(2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol

: 345342-62-3
(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: With toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; water;
DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

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

: 345342-62-3
(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

2: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

3: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4: 66 percent / diethyl ether / 0.5 h / -78 °C

5: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

With hydrogenchloride; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol010089t

Reference yield:

: 345342-61-2
(2R,3R,4S,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-ol

: 345342-62-3
(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

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

2: 66 percent / diethyl ether / 0.5 h / -78 °C

3: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

With Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/ol010089t