4-Nitrophenyl 4,6-O-Benzylidene-alpha-D-mannopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl 4,6-O-Benzylidene-alpha-D-mannopyranoside
• CAS No.: 58056-41-0
• Molecular Formula: C19H19NO8
• Molecular Weight: 389.362
• DSSTox Substance ID: DTXSID60454080
• Nikkaji Number: J1.043.407F
• Mol file: 58056-41-0.mol

Synonyms:58056-41-0;4-Nitrophenyl 4,6-O-Benzylidene-alpha-D-mannopyranoside;4-Nitrophenyl-4,6-O-benzylidene-a-D-mannopyranoside;(4aR,6R,7S,8R,8aS)-6-(4-nitrophenoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;4-Nitrophenyl 4,6-O-benzylidene-a-D-mannopyranoside;SCHEMBL7948314;DTXSID60454080;BGBDVEKOBCWPHZ-VHXLSKCLSA-N;AKOS030242480;s11471;4-Nitrophenyl 4,6-O-Benzylidene-?-D-mannopyranoside;4-Nitrophenyl 4,6-O-Benzylidene- alpha -D-mannopyranoside;4-Nitrophenyl 4,6-O-benzylidene-alpha-D-mannopyranoside?;4-Nitrophenyl 4-O,6-O-benzylidene-alpha-D-mannopyranoside

Chemical Property of 4-Nitrophenyl 4,6-O-Benzylidene-alpha-D-mannopyranoside

Chemical Property:

• Melting Point: 109-111?C
• PSA: 123.20000
• LogP: 2.05770
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 389.11106656
• Heavy Atom Count: 28
• Complexity: 529

Purity/Quality:

95% ^*data from raw suppliers

4-Nitrophenyl4,6-O-Benzylidene-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(C(C(O2)OC3=CC=C(C=C3)[N+](=O)[O-])O)O)OC(O1)C4=CC=CC=C4
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H]([C@@H]([C@H](O2)OC3=CC=C(C=C3)[N+](=O)[O-])O)O)OC(O1)C4=CC=CC=C4
• Uses: 4-Nitrophenyl 4,6-O-Benzylidene-α-D-mannopyranoside (cas# 58056-41-0) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl 4,6-O-Benzylidene-alpha-D-mannopyranoside

There total 2 articles about 4-Nitrophenyl 4,6-O-Benzylidene-alpha-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: 83.0%

benzaldehyde dimethyl acetal (1125-88-8) + 4-nitrophenyl-α-D-mannopyranoside (10357-27-4) → p-nitrophenyl 4,6-O-benzylidene-α-D-mannopyranoside (58056-41-0)

Guidance literature:

With triethylamine; In N-methyl-acetamide; diethyl ether;

Reference yield:

→ (2R,4aR,6R,7S,8R,8aR)-6-(4-Nitro-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (58056-41-0,61169-00-4,61169-04-8,61221-62-3,83167-73-1,85906-27-0,94062-90-5,118396-60-4)

Guidance literature:

aus p-Nitrophenyl-α-D-mannopyranosid nach der Methode von Buchanan,Schwarz, J.Chem.Soc.<1962> 4770;

Reference yield: 60.0%

p-nitrophenyl 4,6-O-benzylidene-α-D-mannopyranoside (58056-41-0) + orthobenzoic acid trimethyl ester (707-07-3) → p-nitrophenyl 2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside (81562-01-8,94063-92-0)

Guidance literature:

toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1016/0008-6215(84)85024-7

upstream raw materials:

benzaldehyde dimethyl acetal

4-nitrophenyl-α-D-mannopyranoside

Downstream raw materials:

p-nitrophenyl 2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside

p-nitrophenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside

p-nitrophenyl 3-O-α-D-mannopyranosyl-α-D-mannopyranoside