allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 263893-88-5
• Molecular Formula: C₅₉H₆₄O₁₂
• Molecular Weight: 965.15

Synonyms:allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

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Technology Process of allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 2 articles about allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 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: 90.0%

(2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (97576-68-6) + 6-O-acetyl-2,3,4-tri-O-benzyl-D-mannopyranosyl dimethylphosphinothioate → allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (263893-88-5)

Guidance literature:

With silver perchlorate; In benzene;

DOI:10.3987/COM-99-S65

Reference yield:

2,3,4-tri-O-benzyl-6-O-acetyl-D-mannopyranose → allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (263893-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -30 °C

1.2: 78 percent / tetrahydrofuran; hexane / 2.5 h / -30 °C

2.1: 90 percent / AgClO₄; MS 4A / benzene

With n-butyllithium; silver perchlorate; In tetrahydrofuran; hexane; benzene; 1.1: Metallation / 1.2: Substitution / 2.1: glycosylation;

DOI:10.3987/COM-99-S65

Reference yield: 100.0%

allyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (263893-88-5) → allyl (2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside (263893-89-6)

Guidance literature:

With sodium methylate; In methanol; for 5h;

DOI:10.3987/COM-99-S65

upstream raw materials:

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

Downstream raw materials:

allyl (2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

C₅₇H₆₃O₁₃P

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