(2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol
• CAS No.: 88559-77-7
• Molecular Formula: C₄₀H₄₆O₁₁
• Molecular Weight: 702.799
• Mol file: 88559-77-7.mol

Synonyms:

Chemical Property of (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol

There total 6 articles about (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (88562-83-8,93661-19-9,98098-96-5) → (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol (88559-77-7,88593-71-9,93661-18-8)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0008-6215(00)81792-9

Reference yield:

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside (57783-66-1) → benzyl 2,3,6-tri-O-benzyl-4-O-β-D-glucopyranosyl-β-D-glucopyranoside (88559-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / sodium cyanoborohydride, molecular sieves 3A, hydrochloric acid/Et₂O / tetrahydrofuran / 1 h / 0 °C

2: 1.) mecuric cyanide; 2.) aq. potassium iodide, 1M sodium methoxide / 1.) benzene, nitromethane, 50 deg C, 24 h; 2.) chloroform, water, methanol, 2 h, rt

With hydrogenchloride; diethyl ether; 3 A molecular sieve; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; potassium iodide; In tetrahydrofuran;

DOI:10.1016/0008-6215(83)84014-2

Reference yield:

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside (74801-06-2) → (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3,4,5-triol (88559-77-7,88593-71-9,93661-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.99 g / silver oxide / dimethylformamide / 18 h

2: silver carbonat, Baker 3 Angstroem molecular sieve / CH₂Cl₂

3: sodium methoxide / methanol

With 3 A molecular sieve; sodium methylate; silver carbonate; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)81792-9

upstream raw materials:

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

benzyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranoside