4-Nitrophenyl4,6-cyclohexylidene-b-D-mannopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl4,6-cyclohexylidene-b-D-mannopyranoside
• CAS No.: 102717-16-8
• Molecular Formula: C₁₈H₂₃NO₈
• Molecular Weight: 381.383
• Mol file: 102717-16-8.mol

Synonyms:Spiro[cyclohexane-1,2'-pyrano[3,2-d][1,3]dioxin],b-D-mannopyranoside deriv.

Chemical Property of 4-Nitrophenyl4,6-cyclohexylidene-b-D-mannopyranoside

Chemical Property:

• Boiling Point: 617.1±55.0 °C(Predicted)
• PKA: 12.53±0.60(Predicted)
• Density: 1.44±0.1 g/cm3(Predicted)
• Solubility.: Chloroform, Ethyl Acetate, Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Nitrophenyl 4,6-cyclohexylidene-b-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: p-Nitrophenyl 4,6-Cyclohexylidene-β-D-mannopyranoside (cas# 102717-16-8) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl4,6-cyclohexylidene-b-D-mannopyranoside

There total 1 articles about 4-Nitrophenyl4,6-cyclohexylidene-b-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: 52.0%

4-nitrophenyl-β-D-mannopyranoside (35599-02-1) + 1-ethoxycyclohexene (1122-84-5) → p-nitrophenyl 4,6-O-cyclohexylidene-β-D-mannopyranoside (102717-16-8)

Guidance literature:

toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(85)85024-2

Reference yield: 59.0%

benzoyl chloride (98-88-4) + p-nitrophenyl 4,6-O-cyclohexylidene-β-D-mannopyranoside (102717-16-8) → p-nitrophenyl 3-O-benzoyl-4,6-O-cyclohexylidene-β-D-mannopyranoside (102717-17-9)

Guidance literature:

With pyridine; at -38 - 20 ℃;

DOI:10.1016/0008-6215(85)85024-2

Reference yield:

p-nitrophenyl 4,6-O-cyclohexylidene-β-D-mannopyranoside (102717-16-8) → p-nitrophenyl 2-O-benzyl-4,6-O-cyclohexylidene-β-D-mannopyranoside (102717-19-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / pyridine / -38 - 20 °C

2: 73 percent / triflic acid / cyclohexane; CH₂Cl₂ / Ambient temperature

3: 69 percent / NaOMe / methanol / 0.5 h / Heating

With pyridine; trifluorormethanesulfonic acid; sodium methylate; In methanol; dichloromethane; cyclohexane;

DOI:10.1016/0008-6215(85)85024-2

upstream raw materials:

4-nitrophenyl-β-D-mannopyranoside

1-ethoxycyclohexene

Downstream raw materials:

p-nitrophenyl 3-O-benzoyl-4,6-O-cyclohexylidene-β-D-mannopyranoside

p-nitrophenyl 2-O-benzyl-4,6-O-cyclohexylidene-β-D-mannopyranoside

p-nitrophenyl 3-O-benzoyl-2-O-benzyl-4,6-O-cyclohexylidene-β-D-mannopyranoside

p-nitrophenyl O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-3)-2-O-benzyl-α-D-mannopyranoside

Refernces