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

Base Information

Chemical Name:methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-glucopyranoside
CAS No.:1443016-89-4
Molecular Formula:C₆₂H₆₆O₁₁
Molecular Weight:987.199
Hs Code.:

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

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

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

There total 4 articles about methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-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: 94.0%

: 20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6
(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

: 1443016-76-9
benzoxazolyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

: 1443016-89-4
methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-glucopyranoside

Guidance literature:: (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol; benzoxazolyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside; In 1,2-dichloro-ethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -78 ℃; for 0.0833333h; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1039/c3ob40667a

Reference yield:

: 20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6
(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

: 92470-93-4
(2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran

: 1443016-89-4
methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-glucopyranoside

: methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α/β-D-mannopyranosyl)-α-D-glucopyranoside

Guidance literature:: With iron(III) chloride; In dichloromethane; at 0 ℃; for 16h; Overall yield = 95 %; Molecular sieve; Inert atmosphere;
DOI:10.1039/c8ob02413h

Reference yield:

: 4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5
2,3,4,6-tetra-O-benzyl-D-mannopyranose

: 1443016-89-4
methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hydroxide / acetone / 2 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: 1,2-dichloro-ethane / 1 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

With potassium hydroxide; In 1,2-dichloro-ethane; acetone;
DOI:10.1039/c3ob40667a