{(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methanol

Base Information

• Chemical Name: {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methanol
• CAS No.: 498554-14-6
• Molecular Formula: C₂₆H₄₄O₇Si₂
• Molecular Weight: 524.802

Synonyms:{(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methanol

Chemical Property of {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methanol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methanol

There total 6 articles about {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methanol 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: 85.0%

(1S,2R,4R,7R,10R)-12,12,14,14-tetraisopropyl-9-methylene-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.02,7]pentadecane (498554-13-5) → {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.02,7]pentadec-9-yl}methanol (498554-14-6)

Guidance literature:

(1S,2R,4R,7R,10R)-12,12,14,14-tetraisopropyl-9-methylene-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadecane; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 23 ℃; for 2h;

With tert.-butylhydroperoxide; sodium hydroxide; In tetrahydrofuran; toluene; at 23 ℃; for 11h;

DOI:10.1016/S0040-4020(02)01329-7

Reference yield:

(1S,2R,4R,7R,10R)-12,12,14,14-tetraisopropyl-9-methylene-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.02,7]pentadecane (498554-13-5) → {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.02,7]pentadec-9-yl}methanol (498554-14-6) + {(1S,2R,4R,7R,9R,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.02,7]pentadec-9-yl}methanol

Guidance literature:

(1S,2R,4R,7R,10R)-12,12,14,14-tetraisopropyl-9-methylene-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadecane; With borane-THF; In tetrahydrofuran; at 0 ℃; for 1.5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 26 ℃; for 11.5h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(02)01329-7

Reference yield:

4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucopyranose → {(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.02,7]pentadec-9-yl}methanol (498554-14-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: titanocene dichloride / toluene / 72 h / 23 °C

2.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C

3.2: 85 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 11 h / 23 °C

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; titanocene dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Swern oxidation / 2.2: Tebbe olefination;

DOI:10.1016/S0040-4020(02)01329-7

upstream raw materials:

(1S,2R,4R,7R,10R)-12,12,14,14-tetraisopropyl-9-methylene-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadecane

4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucono-1,5-lactone

(5aS,5bR,7R,9aR,11aR)-11-(allyloxy)-2,2,4,4-tetraisopropyl-7-phenylhexahydro[1,3]dioxino[4',5':5,6]pyrano[3,4-f] [1,3,5,2,4]trioxadisilepine

Downstream raw materials:

{(1S,2R,4R,7R,9S,10S)-12,12,14,14-tetraisopropyl-4-phenyl-3,5,8,11,13,15-hexaoxa-12,14-disilatricyclo[8.5.0.0^2,7]pentadec-9-yl}methyl trifluoromethanesulfonate

{(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate

(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-10-(tert-butyldimethylsilyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-ene

{(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methanol

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