Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

Base Information

Chemical Name:Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester
CAS No.:718614-01-8
Molecular Formula:C₃₀H₄₃NO₁₁
Molecular Weight:593.672
Hs Code.:

Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

Synonyms:Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

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Chemical Property of Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

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Technology Process of Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

There total 5 articles about Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl 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: 95.0%

: 718614-00-7
Acetic acid (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-ylmethyl ester

: 718614-01-8
Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

Guidance literature:: With acetic acid; at 20 ℃; for 3h;
DOI:10.1016/j.tetlet.2004.04.031

Reference yield:

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

: 718614-01-8
Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 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

6.1: 90 percent / pyridine / 20 °C

7.1: 95 percent / AcOH / 3 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; acetic acid; triethylamine; In tetrahydrofuran; pyridine; 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

: 718614-01-8
Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-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-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 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

5.1: 90 percent / pyridine / 20 °C

6.1: 95 percent / AcOH / 3 h / 20 °C

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