(1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol

Base Information

• Chemical Name: (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol
• CAS No.: 127818-07-9
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.439
• Mol file: 127818-07-9.mol

Synonyms:(1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol

Chemical Property of (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol

There total 3 articles about (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.0^2,7>-tetradecan-12-ol 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: 82.0%

(1R,2S,4R,7R,9S,10R,11S,15R)-9-methoxy-1,13,13-trimethyl-4-phenyl-3,5,8,14-tetraoxa-13-silatetracyclo<8.7.0.02,7011,15>heptadecane (127783-20-4,127854-55-1) → (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.02,7>-tetradecan-12-ol (127818-07-9)

Guidance literature:

With potassium fluoride; dihydrogen peroxide;

DOI:10.1039/c39900000148

Reference yield:

Methyl 4,6-O-Benzylidene-2,3-dideoxy-3,2-C-<(3'R)-3'-hydroxybutan-1'-yl-4'-ylidene>-3-C-methyl-α-D-arabino-hexopyranoside (127910-93-4) → (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.02,7>-tetradecan-12-ol (127818-07-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 1.5 h

2: 82 percent / azoisobutyronitrile, tributylstannane / benzene / 2 h / Heating

3: 69 percent / KF, 30percent aq. H₂O₂ / dimethylformamide / 24 h / Ambient temperature

With dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

(1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.02,7>-tetradec-10-ene (127783-19-1) → (1R,2S,4R,7R,9S,10R,11R,12R)-11-hydroxymethyl-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.7.0.02,7>-tetradecan-12-ol (127818-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / azoisobutyronitrile, tributylstannane / benzene / 2 h / Heating

2: 69 percent / KF, 30percent aq. H₂O₂ / dimethylformamide / 24 h / Ambient temperature

With potassium fluoride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; In N,N-dimethyl-formamide; benzene;

upstream raw materials:

(1R,2S,4R,7R,9S,10R,11S,15R)-9-methoxy-1,13,13-trimethyl-4-phenyl-3,5,8,14-tetraoxa-13-silatetracyclo<8.7.0.0^2,70^11,15>heptadecane

Methyl 4,6-O-Benzylidene-2,3-dideoxy-3,2-C-<(3'R)-3'-hydroxybutan-1'-yl-4'-ylidene>-3-C-methyl-α-D-arabino-hexopyranoside

(1R,2S,4R,7R,9S,12R)-12-<(bromomethyl)dimethylsiloxy>-9-methoxy-1-methyl-4-phenyl-3,5,8-trioxatricyclo<8.4.0.0^2,7>-tetradec-10-ene

Downstream raw materials:

Benzoic acid (R)-1-[(1R,2R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-formyl-1-methyl-cyclohexyl]-allyl ester

Benzoic acid (S)-1-[(1R,2R,3R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-2-triethylsilanyloxymethyl-cyclohexyl]-2-oxo-ethyl ester