tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate
CAS No.:1398229-29-2
Molecular Formula:C₁₇H₂₄INO₄
Molecular Weight:433.286
Hs Code.:

Synonyms:tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

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Chemical Property of tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

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Technology Process of tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

There total 2 articles about tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate 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: 91.0%

: 1398229-07-6
tert-butyl (2S,3R,4E)-2-benzylamino-3,6-dihydroxyhex-4-enoate

: 1398229-29-2
tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

: 1398229-35-0
tert-butyl (2S,3S,4S,5S)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

Guidance literature:: With iodine; potassium carbonate; In dichloromethane; at -20 ℃; for 3h;
DOI:10.1021/jo301178b

Reference yield:

: tert-butyl cis-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-2-carboxylate

: 1398229-29-2
tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / tetrahydrofuran; water / 4.5 h / 20 °C

2: iodine; potassium carbonate / dichloromethane / 3 h / -20 °C

With iodine; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo301178b

Reference yield:

: 1398229-29-2
tert-butyl (2S,3S,4R,5R)-1-benzyl-3-hydroxy-5-hydroxymethyl-4-iodopyrrolidine-2-carboxylate

: 1398229-77-0
tert-butyl (2S,3S,4R,5R)-1-benzyl-3,4-dihydroxy-5-(hydroxymethyl)prolinate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 5 h / 20 °C

2.1: silver(I) acetate / acetic acid / 19 h / 40 °C / Inert atmosphere

2.2: 1 h / 20 °C

With silver(I) acetate; In acetic acid;
DOI:10.1021/jo301178b