(2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

Base Information

Chemical Name:(2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine
CAS No.:141045-69-4
Molecular Formula:C₃₇H₄₇NO₇Si
Molecular Weight:645.868
Hs Code.:

Synonyms:(2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

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Chemical Property of (2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

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Technology Process of (2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

There total 10 articles about (2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine 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: 98.0%

: 141045-68-3
(2S,1'S,2'R,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

: 77-76-9
2,2-dimethoxy-propane

: 141045-69-4
(2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

Guidance literature:: With camphor-10-sulfonic acid; In acetone; for 15h; Ambient temperature;
DOI:10.1021/jo00037a025

Reference yield:

: 6216-63-3
N-Cbz-Prolinol

: 141045-69-4
(2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, 1 h, -45 deg C, 2) CH₂Cl₂, to r.t.

3: 96 percent / pyridine, 4-(dimethylamino)pyridine / 15 h / 70 °C

4: m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / 0 °C

5: (MeO)3P / methanol / 3 h

6: 83 percent / imidazole / dimethylformamide / 5 h / 70 °C

7: 64 percent / OsO₄, N-methylmorpholine N-oxide / H₂O; 2-methyl-propan-2-ol / 15 h / Ambient temperature

8: 98 percent / camphorsulfonic acid / acetone / 15 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/jo00037a025

Reference yield:

: 71461-30-8
(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester

: 141045-69-4
(2S,1'S,2'S,3'S)-N-(Benzoxycarbonyl)-2-<1'-acetoxy-2',3'-O-isopropylidene-2',3'-dihydroxy-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

2: 96 percent / pyridine, 4-(dimethylamino)pyridine / 15 h / 70 °C

3: m-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / 0 °C

4: (MeO)3P / methanol / 3 h

5: 83 percent / imidazole / dimethylformamide / 5 h / 70 °C

6: 64 percent / OsO₄, N-methylmorpholine N-oxide / H₂O; 2-methyl-propan-2-ol / 15 h / Ambient temperature

7: 98 percent / camphorsulfonic acid / acetone / 15 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; camphor-10-sulfonic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/jo00037a025