(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Name:(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:211570-43-3
Molecular Formula:C₃₄H₄₅NO₈Si
Molecular Weight:623.819
Hs Code.:

Synonyms:(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 13 articles about (2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl 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: 91.0%

: 211570-42-2
(2S,3S)-2-[(E)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

: (2S,3S)-2-[(1S,2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

: 211570-43-3
(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; water; In acetone; at 0 ℃;
DOI:10.1039/a802741b

Reference yield:

: 20194-18-7
sodium phenyl-methanolate

: 211570-43-3
(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / tetrahydrofuran / 20 °C

2: Et₃N / CH₂Cl₂ / Heating

3: TsOH / methanol / 20 °C

4: imidazole / dimethylformamide; CH₂Cl₂ / -60 °C

5: 91 percent / OsO₄, NMO, H₂O / acetone / 0 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; water; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1039/a802741b

Reference yield:

: 211518-41-1
(Z)-(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-4-ene-1,3-diol

: 211570-43-3
(2S,3S)-2-[(1R,2S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,2,3-trihydroxy-butyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -60 °C

2: DBU / acetonitrile / 0 °C

3: 1.) methyl 2,2,2-trichloroacetimidate, Et₃N, 2.) PPTS / 1.) MeCN, -20 to -15 deg C, 2.) MeOH, H₂O, 20 deg C

4: 84 percent / H₂O₂ / H₂O; tetrahydrofuran / 0 - 20 °C

5: 92 percent / Bu₄NF / tetrahydrofuran / -5 - 0 °C

6: 88 percent / DIAD, PPh₃ / tetrahydrofuran / 0 °C

7: 90 percent / tetrahydrofuran / 20 °C

8: Et₃N / CH₂Cl₂ / Heating

9: TsOH / methanol / 20 °C

10: imidazole / dimethylformamide; CH₂Cl₂ / -60 °C

11: 91 percent / OsO₄, NMO, H₂O / acetone / 0 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; methyl 2,2,2-trichloroacetimidate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1039/a802741b