O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate

Base Information

• Chemical Name: O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate
• CAS No.: 460745-26-0
• Molecular Formula: C₃₆H₄₀Cl₃NO₇
• Molecular Weight: 705.075

Synonyms:O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate

Chemical Property of O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate

Chemical Property:

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Technology Process of O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate

There total 4 articles about O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate 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%

trichloroacetonitrile (545-06-2) + 2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranose → O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate (460745-26-0)

Guidance literature:

With caesium carbonate; In dichloromethane;

DOI:10.1002/1521-3773(20020617)41

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate (460745-26-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / OsO₄; 4-methylmorpholine N-oxide; H₂O / acetone

2: 99 percent / DCC; DMAP / CH₂Cl₂

3: 83 percent / H₂NNH₂*AcOH / dimethylformamide

4: 87 percent / Cs₂CO₃ / CH₂Cl₂

With dmap; osmium(VIII) oxide; water; hydrazinium monoacetate; caesium carbonate; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/1521-3773(20020617)41

Reference yield:

3,4,6-tri-O-benzyl-D-glucopyranose (20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1) → O-[2-O-(6-heptenoyl)-3,4,6-tri-O-benzyl-D-glucopyranosyl] trichloroacetimidate (460745-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / DCC; DMAP / CH₂Cl₂

2: 83 percent / H₂NNH₂*AcOH / dimethylformamide

3: 87 percent / Cs₂CO₃ / CH₂Cl₂

With dmap; hydrazinium monoacetate; caesium carbonate; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20020617)41

upstream raw materials:

trichloroacetonitrile

3,4,6-tri-O-benzyl-D-glucal

3,4,6-tri-O-benzyl-D-glucopyranose

Downstream raw materials:

Hept-6-enoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,3R,4S,5R)-5-(2-chloro-acetoxy)-3,4-bis-((S)-2-methyl-butyryloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-3-yl ester

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