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

Base Information

Chemical Name:tert-butyl (2S,3S,4R,5R)-1-benzyl-3,4-dihydroxy-5-(hydroxymethyl)prolinate
CAS No.:1398229-77-0
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

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

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Chemical Property of tert-butyl (2S,3S,4R,5R)-1-benzyl-3,4-dihydroxy-5-(hydroxymethyl)prolinate

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Technology Process of tert-butyl (2S,3S,4R,5R)-1-benzyl-3,4-dihydroxy-5-(hydroxymethyl)prolinate

There total 4 articles about tert-butyl (2S,3S,4R,5R)-1-benzyl-3,4-dihydroxy-5-(hydroxymethyl)prolinate 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: 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

Reference yield:

: tert-butyl cis-1-benzyl-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]aziridine-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 4 steps

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

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

3.1: 5 h / 20 °C

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

4.2: 1 h / 20 °C

With iodine; silver(I) acetate; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetic acid;
DOI:10.1021/jo301178b

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 5 h / 20 °C

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

3.2: 1 h / 20 °C

With iodine; silver(I) acetate; potassium carbonate; In dichloromethane; acetic acid;
DOI:10.1021/jo301178b