Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid

Base Information

• Chemical Name: Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid
• CAS No.: 89733-59-5
• Molecular Formula: C₅₄H₆₃NO₁₈
• Molecular Weight: 1014.09

Synonyms:Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid

Chemical Property of Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid

Chemical Property:

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Technology Process of Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid

There total 3 articles about Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid 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: 48.0%

benzyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (35017-04-0) + N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid (82703-91-1) + Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid (89733-59-5)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1016/0008-6215(84)85141-1

Reference yield:

2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure (19342-36-0) → Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid (89733-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether; methanol

2: 94 percent / TiCl₄ / CH₂Cl₂; ethyl acetate / 0 deg C 16 hour, room temp. 5 hour.

3: 48 percent / Hg(CN)2, HgBr₂ / CH₂Cl₂ / 96 h / Ambient temperature

With mercury(II) cyanide; titanium tetrachloride; mercury dibromide; In methanol; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1016/0008-6215(84)85141-1

Reference yield:

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (108740-39-2,6931-68-6,72690-21-2,73208-82-9,108740-37-0,108740-38-1,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,74006-95-4) → Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid (89733-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / TiCl₄ / CH₂Cl₂; ethyl acetate / 0 deg C 16 hour, room temp. 5 hour.

2: 48 percent / Hg(CN)2, HgBr₂ / CH₂Cl₂ / 96 h / Ambient temperature

With mercury(II) cyanide; titanium tetrachloride; mercury dibromide; In dichloromethane; ethyl acetate;

DOI:10.1016/0008-6215(84)85141-1

upstream raw materials:

benzyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

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