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

Base Information

• Chemical Name: methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS No.: 79414-62-3
• Molecular Formula: C₄₂H₅₀O₁₅
• Molecular Weight: 794.85

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

Chemical Property of methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside

There total 3 articles about methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 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: 87.0%

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside (79414-62-3)

Guidance literature:

With N-iodo-succinimide; lanthanum(lll) triflate; In dichloromethane; at 0 ℃; for 1.5h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0030-1259016

Reference yield: 86.4%

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside (79414-62-3)

Guidance literature:

With mercury(II) cyanide; In nitromethane; at 60 ℃; for 4h;

DOI:10.1016/S0008-6215(00)85303-3

Reference yield: 64.0%

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) + O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) → methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside (79414-62-3)

Guidance literature:

With perchloric acid; 4 A molecular sieve; In 1,2-dichloro-ethane; at -10 ℃;

DOI:10.1021/jo051390g

upstream raw materials:

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

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

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

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