methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

Base Information

• Chemical Name: methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside
• CAS No.: 359765-20-1
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

Synonyms:methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

Chemical Property of methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

Chemical Property:

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Technology Process of methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

There total 2 articles about methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside 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: 80.5%

benzyl bromide (100-39-0) + methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside (359765-18-7) → methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside (359765-20-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -10 - 20 ℃; for 3h;

DOI:10.1016/S0008-6215(01)00103-3

Reference yield:

methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,4-furanoside (201788-59-2) → methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside (359765-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 59.7 percent / magnesium / tetrahydrofuran / 14 h / -30 - 20 °C

2: 80.5 percent / NaH / dimethylformamide / 3 h / -10 - 20 °C

With sodium hydride; magnesium; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00103-3

Reference yield: 67.8%

methyl 7-O-allyl-5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside (359765-20-1) → methyl 5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside (359765-21-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; In ethanol; hexane; water; for 4h; Heating;

DOI:10.1016/S0008-6215(01)00103-3

upstream raw materials:

benzyl bromide

methyl 7-O-allyl-5-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,4-furanoside

Downstream raw materials:

methyl 5,6-di-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

(2S,3S)-2,3-Bis-benzyloxy-3-((3aS,4R,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionaldehyde

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