(2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol

Base Information

• Chemical Name: (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol
• CAS No.: 142917-79-1
• Molecular Formula: C₂₁H₂₆BrNO₃
• Molecular Weight: 420.346

Synonyms:(2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol

Chemical Property of (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol

Chemical Property:

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Technology Process of (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol

There total 4 articles about (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol 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: 60.0%

{(R)-1-[(2R,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-allyl}-((S)-1-phenyl-ethyl)-amine (142917-72-4) → (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol (142917-79-1)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; Heating;

DOI:10.1016/S0040-4039(00)92087-2

Reference yield:

(S)-1-phenyl-ethylamine (2627-86-3) → (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol (142917-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / molecular sieves 4A / diethyl ether

2: 1) BF₃*Et₂O / 1) Et₂O, -78 deg C

3: 60 percent / dil. H₂SO₄ / dioxane / Heating

With 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; In 1,4-dioxane; diethyl ether;

DOI:10.1016/S0040-4039(00)92087-2

Reference yield:

(2S,3S)-3-(4-Bromo-benzyloxymethyl)-oxirane-2-carbaldehyde (141277-15-8,141277-16-9,143004-29-9) → (2R,3R,4R)-1-(4-Bromo-benzyloxy)-4-((S)-1-phenyl-ethylamino)-hex-5-ene-2,3-diol (142917-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / molecular sieves 4A / diethyl ether

2: 1) BF₃*Et₂O / 1) Et₂O, -78 deg C

3: 60 percent / dil. H₂SO₄ / dioxane / Heating

With 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; In 1,4-dioxane; diethyl ether;

DOI:10.1016/S0040-4039(00)92087-2

upstream raw materials:

{(R)-1-[(2R,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-allyl}-((S)-1-phenyl-ethyl)-amine

(S)-1-phenyl-ethylamine

(2S,3S)-3-(4-Bromo-benzyloxymethyl)-oxirane-2-carbaldehyde

[1-[(2R,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-meth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine

Downstream raw materials:

(4R,5R,6R)-6-(4-Bromo-benzyloxymethyl)-5-hydroxy-3-((S)-1-phenyl-ethyl)-4-vinyl-[1,3]oxazinan-2-one

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