(2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate

Base Information

Chemical Name:(2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate
CAS No.:1333395-88-2
Molecular Formula:C₂₆H₂₇BrO₅
Molecular Weight:499.401
Hs Code.:

Synonyms:(2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate

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Chemical Property of (2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate

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Technology Process of (2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate

There total 2 articles about (2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate 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: 57.0%

: 1333395-79-1
(2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate

: 1333395-88-2
(2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate

Guidance literature:: (2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;

With water; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
DOI:10.1021/ol2021274

Reference yield:

: 1333395-91-7
1-(naphthalen-2-ylmethoxy)propan-2-one

: 1333395-88-2
(2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trifluoroacetic acid; 9-amino-9-deoxyepicinchonine / tetrahydrofuran / 48 h / 20 °C / Sealed tube

2.1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

With dimethylsulfide borane complex; trifluoroacetic acid; 9-amino-9-deoxyepicinchonine; In tetrahydrofuran; 1.1: Aldol condensation;
DOI:10.1021/ol2021274