(2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal

Base Information

• Chemical Name: (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal
• CAS No.: 111265-96-4
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346

Synonyms:(2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal

Chemical Property of (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal

Chemical Property:

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Technology Process of (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal

There total 7 articles about (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal 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: 100.0%

(2S,3R,4S)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-2-pyrrolidinylcarboxylic acid (191851-84-0) → (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal (111265-96-4)

Guidance literature:

In tetrahydrofuran;

Reference yield: 95.0%

(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester (111193-62-5) → (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal (111265-96-4)

Guidance literature:

With lithium borohydride; In diethyl ether;

DOI:10.1016/S0040-4039(00)95775-7

Reference yield:

N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose (405215-53-4) → (2R,3R,4S)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol 3,4-O-isopropylidene acetal (111265-96-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.3998/ark.5550190.p008.492

upstream raw materials:

(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

(2S,3R,4S)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-2-pyrrolidinylcarboxylic acid

(S)-3,4-Dihydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(R)-4-hydroxy-L-proline ethyl ester

Downstream raw materials:

(3aR,4R,6aS)-2,2-Dimethyl-4-(toluene-4-sulfonyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

(2R,3R,4S)-1-benzyloxycarbonyl-2-hydroxymethylpyrrolidine-3,4-diol

(2R,3R,4S)-1-(benzyloxycarbonyl)-2-<(phosphooxy)methyl>pyrrolidine-3,4-diol

(3aR,4R,6aS)-2,2-Dimethyl-4-phosphonooxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

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