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

Base Information

Chemical Name:(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:312515-21-2
Molecular Formula:C₄₅H₅₉NO₈Si
Molecular Weight:770.051
Hs Code.:

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

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

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

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

There total 20 articles about (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-hydroxymethyl-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:

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

: 312515-21-2
(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol;
DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

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

: 312515-21-2
(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 20 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

14: tetrahydrofuran / -78 °C

15: NaBH₄; CeCl₃ / methanol / -45 °C

16: Et₃N / CH₂Cl₂

17: t-BuOK / tetrahydrofuran

18: 92 percent / OsO₄; NMO / acetone; H₂O

19: NaIO₄ / diethyl ether; H₂O

20: NaBH₄ / ethanol

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; MS 4 Angstroem; boron trifluoride diethyl etherate; potassium tert-butylate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; 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 / 14: Addition / 15: Reduction / 16: Acylation / 17: Cyclization / 18: Oxidation / 19: Oxidation / 20: Reduction;
DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

: 157831-26-0
(3S,4R,5S)-3,4-dibenzyloxy-1-(4-methoxyphenylmethyl)-5-vinylpyrrolidin-2-one

: 312515-21-2
(2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 98 percent / OsO₄; NMO / acetone; H₂O

2: NaIO₄ / diethyl ether; H₂O

3: BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

4: 71 percent / CAN / acetonitrile; H₂O

5: 75 percent / (i-Pr)2NEt / CH₂Cl₂

6: 91 percent / OsO₄; NMO / acetone; H₂O

7: NaIO₄ / diethyl ether; H₂O

8: NaBH₄ / ethanol

9: 100 percent / imidazole / dimethylformamide

10: 99 percent / Et₃N; DMAP / CH₂Cl₂

11: tetrahydrofuran / -78 °C

12: NaBH₄; CeCl₃ / methanol / -45 °C

13: Et₃N / CH₂Cl₂

14: t-BuOK / tetrahydrofuran

15: 92 percent / OsO₄; NMO / acetone; H₂O

16: NaIO₄ / diethyl ether; H₂O

17: NaBH₄ / ethanol

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; potassium tert-butylate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Oxidation / 2: Oxidation / 3: Addition / 4: Oxidation / 5: Etherification / 6: Oxidation / 7: Oxidation / 8: Reduction / 9: Etherification / 10: Acylation / 11: Addition / 12: Reduction / 13: Acylation / 14: Cyclization / 15: Oxidation / 16: Oxidation / 17: Reduction;
DOI:10.1016/S0040-4039(00)01314-9