(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:312514-99-1
Molecular Formula:C₄₄H₅₅NO₈Si
Molecular Weight:754.008
Hs Code.:

(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 13 articles about (2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 99.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 312515-29-0
(3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one

: 312514-99-1
(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

: 160549-10-0
2,3,5-tri-O-benzyl-D-arabinofuranose

: 312514-99-1
(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / MS 4 Angstroem / benzene; CHCl₃ / reflux

2: 70 percent / tetrahydrofuran / -78 - -40 °C

3: 68 percent / PCC; MS 4 Angstroem / CH₂Cl₂

4: 98 percent / OsO₄; NMO / acetone; H₂O

5: NaIO₄ / diethyl ether; H₂O

6: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

7: 71 percent / CAN / acetonitrile; H₂O

8: 75 percent / (i-Pr)2NEt / CH₂Cl₂

9: 91 percent / OsO₄; NMO / acetone; H₂O

10: NaIO₄ / diethyl ether; H₂O

11: NaBH₄ / ethanol

12: 100 percent / imidazole / dimethylformamide

13: 99 percent / Et₃N; DMAP / CH₂Cl₂

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; MS 4 Angstroem; boron trifluoride diethyl etherate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 1: Condensation / 2: Addition / 3: Oxidation / 4: Oxidation / 5: Oxidation / 6: Addition / 7: Oxidation / 8: Etherification / 9: Oxidation / 10: Oxidation / 11: Reduction / 12: Etherification / 13: Acylation;
DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

: 157831-24-8
((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-(4-methoxy-benzyl)-amine

: 312514-99-1
(2S,3R,4S)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 70 percent / tetrahydrofuran / -78 - -40 °C

2: 68 percent / PCC; MS 4 Angstroem / CH₂Cl₂

3: 98 percent / OsO₄; NMO / acetone; H₂O

4: NaIO₄ / diethyl ether; H₂O

5: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

6: 71 percent / CAN / acetonitrile; H₂O

7: 75 percent / (i-Pr)2NEt / CH₂Cl₂

8: 91 percent / OsO₄; NMO / acetone; H₂O

9: NaIO₄ / diethyl ether; H₂O

10: NaBH₄ / ethanol

11: 100 percent / imidazole / dimethylformamide

12: 99 percent / Et₃N; DMAP / CH₂Cl₂

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; MS 4 Angstroem; boron trifluoride diethyl etherate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Addition / 2: Oxidation / 3: Oxidation / 4: Oxidation / 5: Addition / 6: Oxidation / 7: Etherification / 8: Oxidation / 9: Oxidation / 10: Reduction / 11: Etherification / 12: Acylation;
DOI:10.1016/S0040-4039(00)01314-9