Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS No.: 39524-22-6
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 39524-22-6.mol

Synonyms:Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Chemical Property of Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

There total 6 articles about Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-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: 80.0%

Benzaldehyde dipent-4-enyl acetal (2031-48-3) + ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (23339-15-3) → Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (39524-22-6)

Guidance literature:

With N-Bromosuccinimide; camphor-10-sulfonic acid; In acetonitrile; for 0.25h; Ambient temperature;

DOI:10.1039/c39940000749

Reference yield:

ethanol (64-17-5) + C14H16O6S → Aethyl-4,6-O-benzyliden-2,3-dideoxy-α-D-erythro-hex-2-enopyranosid (39524-22-6,52471-77-9,120710-79-4) + C15H18O4

Guidance literature:

With triethylamine; In dichloromethane; at 40 ℃; for 2h; optical yield given as %de;

DOI:10.1016/j.carres.2008.12.015

Reference yield:

benzaldehyde (100-52-7) → Ethyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (39524-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / p-TsOH, molecular sieves 4 Angstroem / hexane / 8 h / 0 °C

2: 80 percent / NBS, CSA / acetonitrile / 0.25 h / Ambient temperature

With N-Bromosuccinimide; 4 A molecular sieve; camphor-10-sulfonic acid; toluene-4-sulfonic acid; In hexane; acetonitrile;

DOI:10.1021/jo00108a056

upstream raw materials:

ethanol

4,6-O-benzylidene-3-O-(allylthioacetyl)-D-allal

Benzaldehyde dipent-4-enyl acetal

ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside