1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

Base Information

• Chemical Name: 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose
• CAS No.: 126456-55-1
• Molecular Formula: C₃₈H₄₂O₈
• Molecular Weight: 626.747

Synonyms:1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

Chemical Property of 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

Chemical Property:

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Technology Process of 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose

There total 5 articles about 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose 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 2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranoside (122622-12-2) → 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (126456-55-1)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂SO₄

2: HBr / acetic acid

3: by a literature procedure

4: by a literature procedure

5: by a literature procedure

With sulfuric acid; hydrogen bromide; In acetic acid;

DOI:10.1016/0008-6215(89)85198-5

Reference yield:

1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose (104486-80-8) → 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (126456-55-1)

Guidance literature:

Multi-step reaction with 4 steps

1: HBr / acetic acid

2: by a literature procedure

3: by a literature procedure

4: by a literature procedure

With hydrogen bromide; In acetic acid;

DOI:10.1016/0008-6215(89)85198-5

Reference yield:

(3aS,5R,6S,7S,7aS)-5-((S)-1,2-Dihydroxy-ethyl)-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (126456-54-0) → 1,2-O-(1-methoxy)ethylidene-3,4,6,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose (126456-55-1)

Guidance literature:

by a literature procedure;

DOI:10.1016/0008-6215(89)85198-5

upstream raw materials:

(3aS,5R,6S,7S,7aS)-5-((S)-1,2-Dihydroxy-ethyl)-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl bromide

methyl 2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranoside

1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

Downstream raw materials:

Acetic acid (2R,3S,4S,5S,6R)-4,5-bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

ethyl 3,4,6,7-tetra-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

(2R,3S,4S,5S,6R)-3,4-Bis-benzyloxy-2-((S)-1,2-bis-benzyloxy-ethyl)-6-ethylsulfanyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran

ethyl O-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-(1-> 2)-O-3,4,6,7-tetra-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

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