(-)-(S)-((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)methanol

Base Information

• Chemical Name: (-)-(S)-((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)methanol
• CAS No.: 848864-32-4
• Molecular Formula: C₃₇H₆₂O₈Si₂
• Molecular Weight: 691.065
• Mol file: 848864-32-4.mol

Synonyms:(-)-(S)-((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)methanol

Chemical Property of (-)-(S)-((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)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(S)-((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)methanol

There total 2 articles about (-)-(S)-((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)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: 75.0%

(-)-((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) → (-)-(S)-((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)methanol (848864-32-4)

Guidance literature:

With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 - 20 ℃;

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) → (-)-(S)-((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)methanol (848864-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / phenylsilane / Mo(CO)6 / tetrahydrofuran / 4 h / Heating

2: 75 percent / K-Selectride / tetrahydrofuran / -78 - 20 °C

With phenylsilane; potassium tri-sec-butyl-borohydride; hexacarbonyl molybdenum; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2004.11.048

Reference yield: 65.0%

(-)-(S)-((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)methanol (848864-32-4) → (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)

Guidance literature:

(-)-(S)-((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)methanol; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 25 ℃; for 1h;

DOI:10.1016/j.tetasy.2004.11.048

upstream raw materials:

(-)-((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

(-)-((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

Downstream raw materials:

(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

(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