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

Base Information

Chemical Name:(2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine
CAS No.:212892-50-7
Molecular Formula:C₃₃H₃₉NO₆
Molecular Weight:545.676
Hs Code.:

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

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Chemical Property of (2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

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Technology Process of (2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

There total 16 articles about (2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine 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: 78.0%

: 212892-11-0
(3aS,4S,6R,6aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

: 212892-50-7
(2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4020(98)00542-0

Reference yield:

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

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

: 212892-50-7
(2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

Guidance literature:: With sodium tetrahydroborate; In diethyl ether; ethanol; at 0 ℃;
DOI:10.1016/S0040-4020(98)00542-0

Reference yield:

: 124665-84-5
(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone

: 212892-50-7
(2R,3R,4S,5S)-N-tert-butoxycarbonyl-3,4-isopropylidenedioxy-2-trityloxymethyl-5-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / tetrahydrofuran / 3 h / -50 - -40 °C

2: 91 percent / NaBH₄ / methanol / 0 - 20 °C

3: 68 percent / MsCl, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

5: 351 mg / NaBH₄ / ethanol; CH₂Cl₂ / 0 °C

With sodium tetrahydroborate; ozone; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(98)00542-0