(4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene

Base Information

• Chemical Name: (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene
• CAS No.: 848864-34-6
• Molecular Formula: C₄₀H₆₈O₉Si₂
• Molecular Weight: 749.146
• Mol file: 848864-34-6.mol

Synonyms:(4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene

Chemical Property of (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene

There total 4 articles about (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene 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: 73.0%

2,2-dimethoxy-propane (77-76-9) + (4aR,6S,7S,8R,8aR)-6-[(S)-((1S,2R,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-2,2-di-tert-butyl-8-triisopropylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol (848864-33-5) → (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene (848864-34-6)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; pH=3;

DOI:10.1016/j.tetasy.2004.11.048

Reference yield:

(-)-((1S,4R,5R)-4-(benzyloxy)-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl)((4aR,8R,8aR)-2,2-di-tert-butyl-8-((triisopropylsilyl)oxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methanone (848864-30-2) → (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene (848864-34-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 55 percent / phenylsilane / Mo(CO)6 / tetrahydrofuran / 4 h / Heating

2.1: 75 percent / K-Selectride / tetrahydrofuran / -78 - 20 °C

3.1: borane-THF / tetrahydrofuran / 0 - 20 °C

3.2: 65 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 1 h / 25 °C

4.1: 73 percent / p-toluenesulfonic acid / 20 °C / pH 3

With borane-THF; phenylsilane; potassium tri-sec-butyl-borohydride; toluene-4-sulfonic acid; hexacarbonyl molybdenum; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2004.11.048

Reference yield:

(-)-((1S,2S,4R,5R)-4-(benzyloxy)-6,8-dioxabicyclo[3.2.1]oct-2-yl)((4aR,8R,8aR)-2,2-di-tert-butyl-8-((triisopropylsilyl)oxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methanone (848864-31-3) → (4aR,5S,8aS,9R,9aR,10aS)-5-((1S,2S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-2,2-di-tert-butyl-7,7-dimethyl-9-triisopropylsilanyloxy-hexahydro-1,3,6,8,10-pentaoxa-2-sila-anthracene (848864-34-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 75 percent / K-Selectride / tetrahydrofuran / -78 - 20 °C

2.1: borane-THF / tetrahydrofuran / 0 - 20 °C

2.2: 65 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 1 h / 25 °C

3.1: 73 percent / p-toluenesulfonic acid / 20 °C / pH 3

With borane-THF; potassium tri-sec-butyl-borohydride; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2004.11.048

upstream raw materials:

2,2-dimethoxy-propane

(4aR,6S,7S,8R,8aR)-6-[(S)-((1S,2R,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-2,2-di-tert-butyl-8-triisopropylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

(-)-((1S,4R,5R)-4-(benzyloxy)-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl)((4aR,8R,8aR)-2,2-di-tert-butyl-8-((triisopropylsilyl)oxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methanone

(-)-((1S,2S,4R,5R)-4-(benzyloxy)-6,8-dioxabicyclo[3.2.1]oct-2-yl)((4aR,8R,8aR)-2,2-di-tert-butyl-8-((triisopropylsilyl)oxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methanone