(E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Base Information

• Chemical Name: (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS No.: 1431373-47-5
• Molecular Formula: C₂₆H₂₈N₂O₁₀
• Molecular Weight: 528.516
• Mol file: 1431373-47-5.mol

Synonyms:(E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Chemical Property of (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

There total 4 articles about (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 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: 81.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + trans-4-hydroxyazobenzene (1689-82-3,20714-70-9,37790-28-6) → (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1431373-47-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; stereospecific reaction; Inert atmosphere;

DOI:10.1002/open.201402010

Reference yield: 81.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + 4-hydroxyazobenzene (1689-82-3) → (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1431373-47-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 6.25h; Inert atmosphere;

DOI:10.3762/bjoc.9.26

Reference yield: 9.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) + trans-4-hydroxyazobenzene (1689-82-3,20714-70-9,37790-28-6) → (E)-p-(phenylazo)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1431373-47-5) + 3,4,6-tri-O-acetyl-1,2-O-(1-E-(p-(phenylazo)phenoxyethylidene))-β-D-mannopyranose + C26H28N2O10

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ijch.201400211

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

4-hydroxyazobenzene

trans-4-hydroxyazobenzene

2,3,4,6-tetra-O-acetyl-D-mannopyranose

Downstream raw materials:

(E)-p-(phenylazo)phenyl α-D-mannopyranoside

(E)-p-(phenylazo)phenyl 6-O-tert-butyldimethylsilyl-α-D-mannopyranoside

(E)-p-(phenylazo)phenyl 6-O-tert-butyldimethylsilyl-2,3-O-(ethylorthoacetyl)-α-D-mannopyranoside

(E)-p-(phenylazo)phenyl 2,3-O-(ethylorthoacetyl)-α-D-mannopyranoside