methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate

Base Information

• Chemical Name: methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate
• CAS No.: 155193-86-5
• Molecular Formula: C₂₂H₃₀O₈
• Molecular Weight: 422.475

Synonyms:methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate

Chemical Property of methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate

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Technology Process of methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate

There total 10 articles about methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate 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: 75.0%

methanol (67-56-1) + 6-benzyloxy-1-bromo-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol (1426261-18-8) → methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate (155193-86-5)

Guidance literature:

With potassium permanganate; sodium hydrogencarbonate; magnesium sulfate; In water; at 0 ℃; for 5h;

DOI:10.1055/s-0032-1317932

Reference yield: 65.0%

(E)-2-Benzyloxycarbonylamino-3-{(4R,5R)-5-[(R)-benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid methyl ester → methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate (155193-86-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In benzene;

DOI:10.1246/cl.1994.129

Reference yield:

4-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannose (132565-90-3) → methyl (6-benzyloxy-4,5:7,8-di-O-isopropylidene-3-deoxy-D-erythro-D-manno-2-keto) octate (155193-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaH / CH₂Cl₂

2: 65 percent / H₂ / 5percent Pd/C / benzene

With hydrogen; sodium hydride; palladium on activated charcoal; In dichloromethane; benzene;

DOI:10.1246/cl.1994.129

upstream raw materials:

4-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannose

5-O-Benzyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol

5-benzyloxy-2-deoxy-3,4:6,7-di-O-isopropylidene-D-erythro-D-manno-1-heptanol

6-benzyloxy-1,2,3-trideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

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