(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

Base Information

• Chemical Name: (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
• CAS No.: 498554-13-5
• Molecular Formula: C₂₆H₄₂O₆Si₂
• Molecular Weight: 506.787

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

trimethylaluminum (75-24-1) + 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,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)

Guidance literature:

trimethylaluminum; With titanocene dichloride; In toluene; at 23 ℃; for 72h;

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; In tetrahydrofuran; toluene; at 0 - 23 ℃;

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,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)

Guidance literature:

Multi-step reaction with 2 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

With oxalyl dichloride; titanocene dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 1.1: Swern oxidation / 2.2: Tebbe olefination;

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

Reference yield:

(2R,4aR,6aR,11aS,11bR)-8,8,10,10-Tetraisopropyl-2-phenyl-6-[((E)-propenyl)oxy]-hexahydro-1,3,5,7,9,11-hexaoxa-8,10-disila-cyclohepta[a]naphthalene → (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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3.57 g / HgCl₂; HgO; H₂O / acetone / 1 h / 25 °C

2.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

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

3.2: 742.4 mg / toluene; tetrahydrofuran / 0 - 23 °C

With oxalyl dichloride; titanocene dichloride; water; dimethyl sulfoxide; triethylamine; mercury dichloride; mercury(II) oxide; In dichloromethane; acetone; toluene; 2.1: Swern oxidation / 3.2: Tebbe olefination;

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

upstream raw materials:

trimethylaluminum

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,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol

(1R,3R,6R,8S,9S,10R)-8-allyl-10-(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decan-9-ol

(1S,2S,3R,5R,8R,10S,12Z)-2-(tert-butyldimethylsilyloxy)-5-phenyl-4,6,9,15-tetraoxatricyclo[8.5.0.0^3,8]pentadec-12-en-14-one

(1S,2R,3R,5R,8R,10S,12Z)-2-(tert-butyldimethylsilyloxy)-14-methylene-5-phenyl-4,6,9,15-tetraoxatricyclo[8.5.0.0^3,8]pentadec-12-ene

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