(1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene

Base Information

• Chemical Name: (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene
• CAS No.: 77144-72-0
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.353
• Mol file: 77144-72-0.mol

Synonyms:(1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene

Chemical Property of (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene

There total 8 articles about (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene 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: 75.0%

acetic anhydride (108-24-7) + (+/-)-(4aα,7α,8aβ,8β)-2-phenyl-4a,7,8,8a-tetrahydro-4H-1,3-benzodioxin-7,8-diol (77144-71-9,119066-23-8) → Acetic acid (4aR,7S,8S,8aR)-7-acetoxy-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-8-yl ester (77144-72-0)

Guidance literature:

In pyridine;

DOI:10.1246/cl.1980.1559

Reference yield: 75.0%

DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol (77144-67-3) → (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene (77144-72-0)

Guidance literature:

DOI:10.1021/jo00156a012

Reference yield:

DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (70838-35-6) → (1SR,3SR,6RS,8SR,9SR,10SR)-9,10-diacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]dec-7-ene (77144-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 25 percent / lithium bromide / dimethylformamide / 20 h / 100 - 105 °C

2: 80 percent / methanolic sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 75 percent

With sodium methylate; lithium bromide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00156a012

upstream raw materials:

DL-(1,3/2,4)-4-(hydroxymethyl)-5-cyclohexene-1,2,3-triol

DL-(1,3/2,4,6)-1,2,3-tri-O-acetyl-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

DL-O-triacetyl-(1,3/2,4)-4-<(benzoyloxy)methyl>-5-cyclohexene-1,2,3-triol

acetic anhydride

Downstream raw materials:

DL-Di-O-acetyl-3,7-O-benzylidene-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

DL-2,3,-Di-O-acetyl-1,7-O-benzylidene-(1,3,4/2,5,6)-4-azido-6-(hydroxymethyl)-1,2,3,5-cyclohexanetetrol

valienamine