[(3R,4S,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)-isoxazolidin-4-yl]-methanol

Base Information

Chemical Name:[(3R,4S,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)-isoxazolidin-4-yl]-methanol
CAS No.:718614-05-2
Molecular Formula:C₃₄H₅₅NO₁₀Si
Molecular Weight:665.897
Hs Code.:

[(3R,4S,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)-isoxazolidin-4-yl]-methanol

Synonyms:[(3R,4S,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)-isoxazolidin-4-yl]-methanol

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Chemical Property of [(3R,4S,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)-isoxazolidin-4-yl]-methanol

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Technology Process of [(3R,4S,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)-isoxazolidin-4-yl]-methanol

There total 5 articles about [(3R,4S,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)-isoxazolidin-4-yl]-methanol 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: 98.0%

: 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

: 718614-05-2
[(3R,4S,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)-isoxazolidin-4-yl]-methanol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.tetlet.2004.04.031

Reference yield:

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

: 718614-05-2
[(3R,4S,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)-isoxazolidin-4-yl]-methanol

Guidance literature:: Multi-step reaction with 5 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

5.1: 98 percent / LiBH₄ / tetrahydrofuran / 20 °C

With 1H-imidazole; osmium(VIII) oxide; lithium borohydride; 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

: 718614-05-2
[(3R,4S,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)-isoxazolidin-4-yl]-methanol

Guidance literature:: Multi-step reaction with 4 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

4.1: 98 percent / LiBH₄ / tetrahydrofuran / 20 °C

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