(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

Base Information

Chemical Name:(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid
CAS No.:140201-72-5
Molecular Formula:C₃₆H₃₉NO₆
Molecular Weight:581.709
Hs Code.:

Synonyms:(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

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Chemical Property of (2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

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Technology Process of (2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

There total 16 articles about (2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid 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: 79.0%

: 140201-71-4
(2S,3S,1'S,2'R,3'S)-3-(Benzyloxy)-2-<1',2',3'-tris(benzyloxy)-3'-carboxypropyl>-N-(trifluoroacetyl)pyrrolidine

: 140201-72-5
(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

Guidance literature:: With barium dihydroxide; In methanol; at 60 ℃; for 3h;
DOI:10.1021/jo00037a043

Reference yield:

: 140201-51-0,140386-66-9
(2R,3S,4S,5R/S)-2,3,4-Tri-O-benzyl-6-heptene-1,2,3,4,5-pentol

: 140201-72-5
(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

Guidance literature:: Multi-step reaction with 16 steps

1: 82 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 24 h

2: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂, 2.) a) -78 deg C, 1 h, b) r.t., 2h

3: 9 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 60 h / -6.5 °C

4: 1. NaH / 1.) DMF, 2.) DMF, r.t., 24 h

5: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂

6: LiAlH₄ / diethyl ether / 24 h / 0 deg C to r.t.

7: 93 percent / PPh₃, DEAD / tetrahydrofuran / a) 0 deg C to r.t., b) r.t., 24 h

8: 92 percent / 25percent HCl / methanol / 2 h / 60 °C

9: 92 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

10: 98 percent / DMAP, pyridine / a) 0 deg C, 1 h, b) 0 deg C to r.t., c) r.t., 18 h

11: 94 percent / hydrazine-hydrate / ethanol / 5 h / Heating

12: 91 percent / DMAP, pyridine / 3 h / Ambient temperature

13: 88 percent / TBAF / tetrahydrofuran / 48 h / Ambient temperature

14: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) a) -78 deg C, 20 min, b) 0 deg C, 20 min

15: 50 percent / 1percent aq. KMnO₄, buffer (1.25M KH₂PO₄/0.244M K₂HPO₄) / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

16: 79 percent / 0.1M Ba(OH)2 / methanol / 3 h / 60 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; chromium chloride; barium dihydroxide; potassium permanganate; lithium aluminium tetrahydride; oxalyl dichloride; buffer (1.25M KH₂PO₄/0.244M K₂HPO₄); tetrabutyl ammonium fluoride; sodium hydride; ozone; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo00037a043

Reference yield:

: 140201-70-3
(2S,3S,1'S,2'R,3'S)-3-(Benzyloxy)-2-<1',2',3'-tris(benzyloxy)-4'-oxobutyl>-N-(trifluoroacetyl)pyrrolidine

: 140201-72-5
(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / 1percent aq. KMnO₄, buffer (1.25M KH₂PO₄/0.244M K₂HPO₄) / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

2: 79 percent / 0.1M Ba(OH)2 / methanol / 3 h / 60 °C

With barium dihydroxide; potassium permanganate; buffer (1.25M KH₂PO₄/0.244M K₂HPO₄); In methanol; tert-butyl alcohol;
DOI:10.1021/jo00037a043