phenyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-β-D-gulopyranoside

Base Information

• Chemical Name: phenyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-β-D-gulopyranoside
• CAS No.: 52443-46-6
• Molecular Formula: C₁₉H₁₇NO₇
• Molecular Weight: 371.346

Synonyms:

Chemical Property of phenyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-β-D-gulopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-β-D-gulopyranoside

There total 3 articles about phenyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-β-D-gulopyranoside 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: 92.0%

(4aR,6S,8aS)-8-Nitro-6-phenoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (39727-46-3) → phenyl 2,3-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-β-D-allopyranoside (52443-46-6,113473-36-2,125517-04-6)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; for 0.5h;

DOI:10.1016/0008-6215(87)80183-0

Reference yield: 43.0%

phenyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranoside (39727-45-2) → phenyl 4,6-O-benzylidene-3-deoxy-3-C-nitro-β-D-glucopyranoside (52443-50-2) + phenyl 2,3-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-β-D-allopyranoside (52443-46-6,113473-36-2,125517-04-6)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; for 0.5h; Product distribution; other α-nitroalkenes to give α-nitroepoxides;

DOI:10.1016/0008-6215(87)80183-0

Reference yield:

phenyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-β-D-threo-hex-2-enopyranoside (39727-46-3,119125-08-5,125517-03-5) → phenyl 2,3-anhydro-4,6-O-benzylidene-3-C-nitro-β-D-gulopyranoside (52443-46-6,113473-36-2,125517-04-6)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; for 30h; Yield given;

DOI:10.1016/0008-6215(89)85067-0

upstream raw materials:

(4aR,6S,8aS)-8-Nitro-6-phenoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

phenyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranoside

phenyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-β-D-threo-hex-2-enopyranoside

Downstream raw materials:

1,5-anhydro-4,6-O-benzylidene-2-bromo-2-deoxy-D-erythro-hex-1-en-3-ulose

phenyl 4,6-O-benzylidene-3-deoxy-3-C-nitro-β-D-glucopyranoside

1,5-anhydro-4,6-O-benzylidene-2-chloro-2-deoxy-D-erythro-hex-1-en-3-ulose

1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-iodo-D-erythro-hex-1-en-3-ulose

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