methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside
• CAS No.: 40653-16-5
• Molecular Formula: C₃₀H₃₄O₆
• Molecular Weight: 490.596

Synonyms:methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside

Chemical Property:

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Technology Process of methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside

There total 3 articles about methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside 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:

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside (40653-16-5)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -25 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02620

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (34212-64-1,641635-63-4) → methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside (40653-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2-Iodobenzoic acid / acetonitrile / 6 h / 55 °C

2: sodium hexamethyldisilazane / tetrahydrofuran / -25 - 20 °C / Inert atmosphere

With 2-Iodobenzoic acid; sodium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; 2: |Wittig Olefination;

DOI:10.1021/acs.orglett.5b02620

Reference yield:

→ methyl 2,3,4-tri-O-benzyl-7-O-methyl-6-deoxy-α-D-manno-hept-6-enopyranoside (40653-16-5)

Guidance literature:

Pyranosid (III), Methoxymethyltriphenylphosphoran;

upstream raw materials:

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

(methoxymethyl)triphenylphosphonium chloride

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside

2-((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)ethanol

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

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

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