{(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

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}methyl trifluoromethanesulfonate
• CAS No.: 498554-18-0
• Molecular Formula: C₂₇H₄₃F₃O₉SSi₂
• Molecular Weight: 656.865

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}methyl trifluoromethanesulfonate

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}methyl trifluoromethanesulfonate

Chemical Property:

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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}methyl trifluoromethanesulfonate

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}methyl trifluoromethanesulfonate 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: 98.0%

trifluoromethylsulfonic anhydride (358-23-6) + {(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,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}methyl trifluoromethanesulfonate (498554-18-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

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}methyl trifluoromethanesulfonate (498554-18-0)

Guidance literature:

Multi-step reaction with 4 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

4.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; 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

Reference yield:

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 (498554-12-4) → {(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}methyl trifluoromethanesulfonate (498554-18-0)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 23 °C

2.2: 85 percent / aq. NaOH; TBHP / tetrahydrofuran; toluene / 11 h / 23 °C

3.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; titanocene dichloride; In tetrahydrofuran; dichloromethane; toluene; 1.2: Tebbe olefination;

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

upstream raw materials:

trifluoromethylsulfonic anhydride

{(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

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

(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

Downstream raw materials:

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

{(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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