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

Base Information

• Chemical Name: (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol
• CAS No.: 345342-56-5
• Molecular Formula: C₂₇H₃₄O₆
• Molecular Weight: 454.563
• Mol file: 345342-56-5.mol

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

Chemical Property of (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol

There total 2 articles about (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol 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: 66.0%

methyllithium (917-54-4) + (2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one (345342-55-4) → (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol (345342-56-5) + (2R,3S,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol

Guidance literature:

In diethyl ether;

DOI:10.1016/S0040-4039(01)00355-0

Reference yield:

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) → (2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol (345342-56-5)

Guidance literature:

Multi-step reaction with 4 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

With hydrogenchloride; 3 A molecular sieve; sodium hydride; sodium cyanoborohydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol010089t

Reference yield: 100.0%

(2R,3R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3-ol (345342-56-5) → (2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol (345342-62-3)

Guidance literature:

With toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; water;

DOI:10.1016/S0040-4039(01)00355-0

upstream raw materials:

methyllithium

(2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

Downstream raw materials:

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

nafuredin

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

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