(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

Base Information

Chemical Name:(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine
CAS No.:212892-15-4
Molecular Formula:C₃₆H₄₃NO₆
Molecular Weight:585.741
Hs Code.:

Synonyms:(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

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Technology Process of (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

There total 14 articles about (2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine 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: 30.0%

: (3aS,4S,6R,6aR)-4-Formyl-2,2-dimethyl-6-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

: 762-72-1
allyl-trimethyl-silane

: 212892-15-4
(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(00)92240-8

Reference yield:

: 212892-12-1
tert-butyl (3aS,4R,6R,6aR)-4-{{[(tert-butyl)dimethylsilyl]oxy}methyl}tetrahydro-2,2-dimethyl-6-[(trityloxy)methyl]-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

: 212892-15-4
(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

2: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, -20 deg C to rt

3: 363 mg / diethyl ether / 1 h / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether;
DOI:10.1016/S0040-4020(98)00542-0

Reference yield:

: 212892-52-9
(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

: 212892-15-4
(2R,3R,4S,5R)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-((1S)-1-hydroxy-3-butenyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, -20 deg C to rt

2: 363 mg / diethyl ether / 1 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In diethyl ether;
DOI:10.1016/S0040-4020(98)00542-0