Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester

Base Information

• Chemical Name: Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester
• CAS No.: 207516-43-6
• Molecular Formula: C₁₈H₂₂BrNO₆
• Molecular Weight: 428.28

Synonyms:Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester

Chemical Property of Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester

Chemical Property:

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Technology Process of Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester

There total 5 articles about Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl 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: 99.0%

Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-5-((S)-2-acetoxy-2-phenyl-acetylamino)-4-benzyloxymethyl-2-bromo-cyclopentyl ester (207516-40-3) → Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester (207516-43-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 4h; Ambient temperature;

DOI:10.1021/jo980050a

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester (207516-43-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-Bu₄NIO₄, 2.) Na/Hg / 1.) MeOH, -20 deg C, 24 h, 2.) THF, MeOH, 0 deg C, 8 h

2: 85 percent / NBS / dioxane; H₂O / 18 h / Ambient temperature

3: 94 percent / DMAP

4: 99 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

With dmap; sodium amalgam; N-Bromosuccinimide; hydrogen; tetrabutylammonium periodite; palladium dihydroxide; In 1,4-dioxane; ethanol; water;

DOI:10.1021/jo980050a

Reference yield:

(2S)-(+)-2-hydroxy-2-phenylacetohydroxamic acid (124097-40-1) → Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-2-bromo-4-hydroxymethyl-5-phenylacetylamino-cyclopentyl ester (207516-43-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-Bu₄NIO₄, 2.) Na/Hg / 1.) MeOH, -20 deg C, 24 h, 2.) THF, MeOH, 0 deg C, 8 h

2: 85 percent / NBS / dioxane; H₂O / 18 h / Ambient temperature

3: 94 percent / DMAP

4: 99 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

With dmap; sodium amalgam; N-Bromosuccinimide; hydrogen; tetrabutylammonium periodite; palladium dihydroxide; In 1,4-dioxane; ethanol; water;

DOI:10.1021/jo980050a

upstream raw materials:

Acetic acid (1S,2S,3R,4R,5S)-3-acetoxy-5-((S)-2-acetoxy-2-phenyl-acetylamino)-4-benzyloxymethyl-2-bromo-cyclopentyl ester

5-(benzyloxymethyl)cyclopentadiene

(2S)-(+)-2-hydroxy-2-phenylacetohydroxamic acid

(S)-N-((1S,2R,3R,4S,5S)-2-Benzyloxymethyl-4-bromo-3,5-dihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

Downstream raw materials:

Acetic acid (1R,2R,3R,4S,5R)-2,4-diacetoxy-1-acetoxymethyl-3-bromo-5-phenylacetylamino-cyclopentyl ester

(3aR,4R,5R,6S,6aS)-6-Bromo-4-hydroxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylamino)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5-diol

1-((1R,2R,3R,4R,5S)-4-Bromo-2,3,5-trihydroxy-2-hydroxymethyl-cyclopentyl)-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-thiourea

Acetic acid (1S,2S,3R,5S)-3-acetoxy-2-bromo-4-methylene-5-phenylacetylamino-cyclopentyl ester

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