(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

Base Information

Chemical Name:(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester
CAS No.:718613-99-1
Molecular Formula:C₃₅H₅₅NO₁₁Si
Molecular Weight:693.907
Hs Code.:

(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

Synonyms:(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

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Chemical Property of (3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

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Technology Process of (3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

There total 4 articles about (3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl 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: 75.0%

: 71553-88-3
metrhyl (Z)-6,7-dideoxyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-5-enopyranuronate

: 718613-98-0
C₂₀H₃₃NO₄Si

: 718613-99-1
(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

Guidance literature:: With triethylamine; In benzene; for 48h; Heating;
DOI:10.1016/j.tetlet.2004.04.031

Reference yield:

: 213767-09-0
2,3-O-isopropylidene-L-erythrofuranose

: 718613-99-1
(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / n-BuLi / tetrahydrofuran / -78 °C

2.1: 92 percent / imidazole / dimethylformamide / 20 °C

3.1: OsO₄; NMO / acetone; H₂O / 5 h / 20 °C

3.2: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

3.3: 93 percent / Et₃N / CH₂Cl₂ / 20 °C

4.1: 75 percent / NEt₃ / benzene / 48 h / Heating

With 1H-imidazole; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; benzene; 1.1: Wittig reaction;
DOI:10.1016/j.tetlet.2004.04.031

Reference yield:

: 114817-96-8,127758-25-2,99902-67-7
(4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane

: 718613-99-1
(3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / imidazole / dimethylformamide / 20 °C

2.1: OsO₄; NMO / acetone; H₂O / 5 h / 20 °C

2.2: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

2.3: 93 percent / Et₃N / CH₂Cl₂ / 20 °C

3.1: 75 percent / NEt₃ / benzene / 48 h / Heating

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; triethylamine; In water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/j.tetlet.2004.04.031