methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Base Information

• Chemical Name: methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside
• CAS No.: 211231-30-0
• Molecular Formula: C₃₉H₄₄O₇
• Molecular Weight: 624.774

Synonyms:methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Chemical Property of methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Chemical Property:

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Technology Process of methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

There total 4 articles about methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 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: 97.2%

benzyl chloride (100-44-7) + methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-29-7) → methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-30-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 8h;

DOI:10.1016/S0008-6215(98)00037-8

Reference yield: 94.0%

benzyl bromide (100-39-0) + methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-29-7) → methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-30-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00271-7

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) → methyl 7-O-allyl-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (211231-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Mg / tetrahydrofuran / 20 - 24 °C

2: 94 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature

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

DOI:10.1016/S0008-6215(98)00271-7

upstream raw materials:

benzyl chloride

methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

benzyl bromide

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-7-O-dibenzyloxyphosphoryl-L-glycero-α-D-manno-heptopyranoside

3-[(S)-2-Benzyloxy-2-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide

methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

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