(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine

Base Information

• Chemical Name: (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine
• CAS No.: 1030313-77-9
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374

Synonyms:(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine

Chemical Property of (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine

Chemical Property:

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Technology Process of (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine

There total 2 articles about (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine 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: 37.0%

Methoxyallene (13169-00-1) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (3R,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine (1030313-79-1) + (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine (1030313-77-9)

Guidance literature:

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone; With trimethylaluminum; In hexane; dichloromethane; at 0 ℃; for 1h;

Methoxyallene; In hexane; dichloromethane; at 0 - 8 ℃; for 50h; Further stages.;

DOI:10.1002/ejoc.200700724

Reference yield: 37.0%

Methoxyallene (13169-00-1) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (3R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine + (3R,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine (1030313-79-1) + (3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine (1030313-77-9) + (3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine (1030313-78-0)

Guidance literature:

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.333333h;

Methoxyallene; In dichloromethane; at -78 - -65 ℃; for 1h; Further stages.;

DOI:10.1002/ejoc.200700724

Reference yield:

(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methoxy-4-methyleneisoxazolidine (1030313-77-9) + allyl triflate (41029-45-2) → CF3O3S(1-)*C20H28NO4(1+)

Guidance literature:

In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200700724

upstream raw materials:

Methoxyallene

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

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