(3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol

Base Information

• Chemical Name: (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol
• CAS No.: 260369-35-5
• Molecular Formula: C₄₀H₄₉NO₅Si₂
• Molecular Weight: 680.004
• Mol file: 260369-35-5.mol

Synonyms:(3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol

Chemical Property of (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol

There total 4 articles about (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol 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:

[4S(4α,5β,5aβ,5bα,8aα)]-hexahydro-4,5-di(t-butyldiphenylsilyloxy)-pyrrolo[1,2-b]furo[2,3-d]isoxazol-7(3H)one (260369-34-4) → (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol (260369-35-5)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 4h;

DOI:10.1016/S0040-4020(99)01001-7

Reference yield:

(3S,4S)-(+)-3,4-bis<(tert-butyldiphenylsilyl)oxy>-3,4-dihydro-2H-pyrrole 1-oxide (154878-81-6) → (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol (260369-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 58 percent / trimethylsilyl triflate / CH₂Cl₂ / 1.5 h / -20 °C

2.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 0.75 h / 20 °C

2.2: 92 percent / silica gel / cyclohexane; ethyl acetate

3.1: DIBAH / diethyl ether; hexane / 4 h / -78 °C

With trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; trifluoroacetic acid; In diethyl ether; hexane; dichloromethane; water; 1.1: Condensation / 2.1: Hydrolysis / 2.2: Cyclization / 3.1: Reduction;

DOI:10.1016/S0040-4020(99)01001-7

Reference yield:

[2'S-[2'α,3'α,4'β(5RS*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone → (3aR,3bS,4S,5S,7aR)-4,5-Bis-(tert-butyl-diphenyl-silanyloxy)-octahydro-3,7-dioxa-6a-aza-cyclopenta[a]pentalen-2-ol (260369-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 20 °C

1.2: 56 percent / silica gel / cyclohexane; ethyl acetate

2.1: DIBAH / diethyl ether; hexane / 4 h / -78 °C

With diisobutylaluminium hydride; trifluoroacetic acid; In diethyl ether; hexane; dichloromethane; water; 1.1: Hydrolysis / 1.2: Cyclization / 2.1: Reduction;

DOI:10.1016/S0040-4020(99)01001-7

upstream raw materials:

[4S(4α,5β,5aβ,5bα,8aα)]-hexahydro-4,5-di(t-butyldiphenylsilyloxy)-pyrrolo[1,2-b]furo[2,3-d]isoxazol-7(3H)one

(3S,4S)-(+)-3,4-bis<(tert-butyldiphenylsilyl)oxy>-3,4-dihydro-2H-pyrrole 1-oxide

[2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone