p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• CAS No.: 14675-52-6
• Molecular Formula: C₁₆H₁₇NO₈
• Molecular Weight: 351.313

Synonyms:p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

Chemical Property of p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

Chemical Property:

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Technology Process of p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

There total 3 articles about p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-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: 40.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + D-glucal triacetate (2873-29-2) → p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (14675-51-5,56196-13-5) + p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (14675-52-6,56196-13-5)

Guidance literature:

In chlorobenzene; for 15h; Heating;

DOI:10.1080/00397919508011424

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4,6-di-O-acetyl-3-O-D-glucal (118356-98-2) → p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (14675-51-5,56196-13-5) + p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (14675-52-6,56196-13-5)

Guidance literature:

With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 24h; optical yield given as %de; stereoselective reaction;

DOI:10.1016/j.tet.2011.11.084

Reference yield:

→ p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside (14675-52-6,56196-13-5)

Guidance literature:

3,4,6-Tri-O-acetyl-D-glucal (0.5 Mol), 4-Nitrophenol (1.95 Mol, Rohprod.), Bzl. (4h, Siedetemp.) ;

upstream raw materials:

4-nitro-phenol

D-glucal triacetate

4,6-di-O-acetyl-3-O-D-glucal

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