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

Base Information

• Chemical Name: [2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone
• CAS No.: 260369-33-3
• Molecular Formula: C₄₃H₅₅NO₅Si₃
• Molecular Weight: 750.17
• Mol file: 260369-33-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about [2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone 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: 58.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (3S,4S)-(+)-3,4-bis<(tert-butyldiphenylsilyl)oxy>-3,4-dihydro-2H-pyrrole 1-oxide (154878-81-6) → [2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone (260369-33-3) + [2'S-[2'α,3'α,4'β(5S*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 1.5h;

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

Reference yield: 92.0%

[2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone (260369-33-3) → [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)

Guidance literature:

[2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone; With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 0.75h;

With silica gel; In cyclohexane; ethyl acetate;

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

Reference yield:

[2'S-[2'α,3'α,4'β(5R*)]]-5-[1'-trimethylsilyloxy-3',4'-di(t-butyldiphenylsilyloxy)-2'-pyrrolidinyl]-2(5H)-furanone (260369-33-3) → [1S(1α,2β,7β,8α,8aα)]-1,2-di(t-butyldiphenylsilyloxy)indolizidine-7,8-diol

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 92 percent / silica gel / cyclohexane; ethyl acetate

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

3.1: 0.106 g / hydrogen / Pd(OH)2/C / methanol; H₂O / 12 h / 2327.17 Torr

With hydrogen; diisobutylaluminium hydride; trifluoroacetic acid; palladium dihydroxide; In methanol; diethyl ether; hexane; dichloromethane; water; 1.1: Hydrolysis / 1.2: Cyclization / 2.1: Reduction / 3.1: Cyclization;

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

upstream raw materials:

(furan-2-yloxy)-trimethylsilane

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

Downstream 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

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