(2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate

Base Information

• Chemical Name: (2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate
• CAS No.: 1333395-79-1
• Molecular Formula: C₂₆H₂₅BrO₅
• Molecular Weight: 497.386
• Mol file: 1333395-79-1.mol

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

Chemical Property of (2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate

There total 1 articles about (2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate 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:

1-(naphthalen-2-ylmethoxy)propan-2-one (1333395-91-7) + ethyl 3-bromo-cinnamate (24398-80-9) → (2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate (1333395-79-1) + (2SR,3RS)-ethyl 2-(3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate

Guidance literature:

With trifluoroacetic acid; 9-amino-9-deoxyepicinchonine; In tetrahydrofuran; at 20 ℃; for 48h; optical yield given as %ee; diastereoselective reaction; Sealed tube;

DOI:10.1021/ol2021274

Reference yield: 63.0%

(2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate (1333395-79-1) → (2R,3R)-ethyl 2-(3-bromophenethyl)-2,3-dihydroxy-4-oxopentanoate (1333395-86-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; under 760.051 Torr;

DOI:10.1021/ol2021274

Reference yield: 57.0%

(2R,3R)-ethyl 2-((E)-3-bromostyryl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate (1333395-79-1) → (2R,3S,4R)-ethyl 2-((E)-3-bromostyryl)-2,4-dihydroxy-3-(naphthalen-2-ylmethoxy)pentanoate (1333395-88-2)

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

upstream raw materials:

1-(naphthalen-2-ylmethoxy)propan-2-one

ethyl 3-bromo-cinnamate

Downstream raw materials:

(2R,3R)-ethyl 2-(3-bromophenethyl)-2,3-dihydroxy-4-oxopentanoate

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

(2R,3R)-ethyl 2-((2S,3R)-3-(3-bromophenyl)oxiran-2-yl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate

(2R,3R)-ethyl 2-((1S,2S)-2-(3-bromophenyl)-1,2-dihydroxyethyl)-2-hydroxy-3-(naphthalen-2-ylmethoxy)-4-oxopentanoate