methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside

Base Information

• Chemical Name: methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside
• CAS No.: 80018-97-9
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.38

Synonyms:methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside

Chemical Property of methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside

Chemical Property:

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Technology Process of methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside

There total 4 articles about methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-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: 78.0%

methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-α-D-allopyranoside (80018-96-8) → methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside (80018-97-9)

Guidance literature:

With thionyl chloride; In pyridine; for 2.5h; Ambient temperature;

DOI:10.1016/S0008-6215(00)81871-6

Reference yield:

(2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine (68366-59-6) → methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside (80018-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / benzene / 64 h / Ambient temperature

2: 100 percent / pyridine; acetic anhydride / 15 h / Ambient temperature

3: 78 percent / thionyl chloride / pyridine / 2.5 h / Ambient temperature

With thionyl chloride; In pyridine; acetic anhydride; benzene;

DOI:10.1016/S0008-6215(00)81871-6

Reference yield:

methyl 3-C-allyl-4,6-O-benzylidene-α-D-allopyranoside (80018-95-7) → methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside (80018-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine; acetic anhydride / 15 h / Ambient temperature

2: 78 percent / thionyl chloride / pyridine / 2.5 h / Ambient temperature

With thionyl chloride; In pyridine; acetic anhydride;

DOI:10.1016/S0008-6215(00)81871-6

upstream raw materials:

methyl 2-O-acetyl-3-C-allyl-4,6-O-benzylidene-α-D-allopyranoside

(2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

methyl 3-C-allyl-4,6-O-benzylidene-α-D-allopyranoside

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

methyl 3-C-allyl-6-O-benzoyl-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

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