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

Base Information

• Chemical Name: (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one
• CAS No.: 312515-29-0
• Molecular Formula: C₃₉H₄₇NO₆Si
• Molecular Weight: 653.891

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

Chemical Property of (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one

There total 12 articles about (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-3-hydroxy-1-methoxymethoxy-propyl)-pyrrolidin-2-one (1054655-54-7) → (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one (312515-29-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one (312515-29-0)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; MS 4 Angstroem; boron trifluoride diethyl etherate; 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;

DOI:10.1016/S0040-4039(00)01314-9

Reference yield:

(3S,4R,5S)-3,4-dibenzyloxy-1-(4-methoxyphenylmethyl)-5-vinylpyrrolidin-2-one (157831-26-0) → (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one (312515-29-0)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In 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;

DOI:10.1016/S0040-4039(00)01314-9

upstream raw materials:

tert-butylchlorodiphenylsilane

(3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-3-hydroxy-1-methoxymethoxy-propyl)-pyrrolidin-2-one

2,3,5-tri-O-benzyl-D-arabinofuranose

(3S,4R,5S)-3,4-dibenzyloxy-1-(4-methoxyphenylmethyl)-5-vinylpyrrolidin-2-one

Downstream raw materials:

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

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

{(1S,2R,3R,4S)-2,3-Bis-benzyloxy-1-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-4-hydroxy-hex-5-enyl}-carbamic acid tert-butyl ester

(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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