tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

Base Information

Chemical Name:tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate
CAS No.:1398229-53-2
Molecular Formula:C₁₉H₂₆INO₅
Molecular Weight:475.324
Hs Code.:

Synonyms:tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

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Chemical Property of tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

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Technology Process of tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

There total 2 articles about tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate 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:

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

: 1398229-53-2
tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 5 h / 20 °C

With iodine; potassium carbonate; In dichloromethane;
DOI:10.1021/jo301178b

Reference yield:

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

: 1398229-53-2
tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 5 h / 20 °C

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

Reference yield: 94.0%

: 1398229-53-2
tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate

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

Guidance literature:: tert-butyl (2S,3S,4R,5R)-5-acetoxymethyl-1-benzyl-3-hydroxy-4-iodoprolinate; With silver(I) acetate; In acetic acid; at 40 ℃; for 19h; Inert atmosphere;

With potassium carbonate; In methanol; at 20 ℃; for 1h;
DOI:10.1021/jo301178b