(1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane

Base Information

• Chemical Name: (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane
• CAS No.: 114779-35-0
• Molecular Formula: C₂₈H₂₈O₅
• Molecular Weight: 444.527
• Mol file: 114779-35-0.mol

Synonyms:(1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane

Chemical Property of (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane

There total 6 articles about (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.0^2.7>undecane 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: 84.0%

(1R,3R,6R,9S,10S)-9,10-dibenzyloxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-7-ene (114779-28-1) → (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.02.7>undecane (114779-35-0)

Guidance literature:

With disodium hydrogenphosphate; sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In water; 1,2-dichloro-ethane; at 50 ℃; for 23h;

DOI:10.1039/P19880002675

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.02.7>undecane (114779-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / PTSA / dimethylformamide / 4.5 h / 60 °C / 15 - 20 Torr

2: 92 percent / sodium hydride / dimethylformamide / 0 deg C, 30 min, 0 deg C, 1.5 h

3: 84 percent / MCPBA, 1M Na₂HPO₄, 1M NaH₂PO₄ / H₂O; 1,2-dichloro-ethane / 23 h / 50 °C

With disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1039/P19880002675

Reference yield:

(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (97747-51-8) → (1R,2S,5R,7R,8R,9R,10R)-8,9-dibenzyloxy-5-phenyl-4,6,11-trioxatricyclo<8.1.0.02.7>undecane (114779-35-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 28.4 percent / lithium bromide monohydrate / dimethylformamide / 30 h / 105 °C

2: 1.) sodium methoxide, 2.) Amberlite IR-120B resin / methanol / 1 h / 0 °C

3: 96 percent / PTSA / dimethylformamide / 4.5 h / 60 °C / 15 - 20 Torr

4: 92 percent / sodium hydride / dimethylformamide / 0 deg C, 30 min, 0 deg C, 1.5 h

5: 84 percent / MCPBA, 1M Na₂HPO₄, 1M NaH₂PO₄ / H₂O; 1,2-dichloro-ethane / 23 h / 50 °C

With disodium hydrogenphosphate; sodium dihydrogenphosphate; Amberlite IR-120B resin; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1039/P19880002675

upstream raw materials:

(1R,3R,6R,9S,10S)-9,10-dibenzyloxy-3-phenyl-2,4-dioxabicyclo<4.4.0>dec-7-ene

benzaldehyde dimethyl acetal

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

(-)-(1R,2R,3R,4S)-1-(hydroxymethyl)cyclohex-5-ene-2,3,4-triol

Downstream raw materials:

methyl 4-deoxy-4-<(1S)-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-hydroxymethyl-1-cyclohexylamino>-α-D-glucopyranoside octa-acetate

methyl 4-deoxy-4-<(1S)-(1,3,5/2,4,6)-2,3,4,5-tetrahydroxy-6-hydroxymethyl-1-cyclohexylamino>-α-D-glucopyranoside octa-acetate