methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS No.: 845669-56-9
• Molecular Formula: C₁₅H₁₅NO₄
• Molecular Weight: 273.288

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

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

Chemical Property:

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

There total 3 articles about methyl 4,6-O-benzylidene-2-C-cyano-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: 93.0%

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside (66008-34-2) + potassium cyanide (151-50-8) → methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (845669-56-9)

Guidance literature:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside; potassium cyanide; With Amberlite IR-120; In water; acetonitrile; at 4 ℃; for 0.5h;

With triethylamine; In water; acetone; at 20 ℃; for 0.2h;

DOI:10.1016/j.carres.2004.10.018

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside (66008-34-2) + potassium cyanide (151-50-8) → methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (845669-56-9) + (2R,4aR,6S,7R,8S,8aS)-6-Methoxy-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7-carbonitrile

Guidance literature:

With Amberlite IR-120; In water; acetonitrile; at 4 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1016/j.carres.2004.10.018

Reference yield:

(2R,4aR,6S,8R,8aS)-6-Methoxy-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol → methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (845669-56-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / MsCl; Et₃N / CH₂Cl₂ / 0.25 h / -20 °C

2.1: Amberlite IR-120 / H₂O; acetonitrile / 0.5 h / 4 °C

2.2: 93 percent / Et₃N / acetone; H₂O / 0.2 h / 20 °C

With Amberlite IR-120; methanesulfonyl chloride; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.carres.2004.10.018

upstream raw materials:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside

potassium cyanide

Downstream raw materials:

C₁₄H₁₁NO₃OCH₄O

C₁₄H₁₁NO₃OCH₄O

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-formyl-α-D-erythro-hex-2-enopyranoside

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