4,5-Dihydroxy-4-(hydroxymethyl)cyclopentene-3-one

Base Information

• Chemical Name: 4,5-Dihydroxy-4-(hydroxymethyl)cyclopentene-3-one
• CAS No.: 57236-37-0
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.127

Synonyms:4,5-Dihydroxy-4-(hydroxymethyl)cyclopentene-3-one;4,5-Dihydroxy-5-hydroxymethyl-2-cyclopenten-1-one;Antibiotic C-2554B;C-2554B

Chemical Property of 4,5-Dihydroxy-4-(hydroxymethyl)cyclopentene-3-one

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

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Technology Process of 4,5-Dihydroxy-4-(hydroxymethyl)cyclopentene-3-one

There total 136 articles about 4,5-Dihydroxy-4-(hydroxymethyl)cyclopentene-3-one 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: 93.0%

4,5,6-tri-O-acetylpentenomycin I (54274-81-6) → (-)-pentenomycin (49644-25-9,57236-37-0)

Guidance literature:

With trifluoroacetic acid; In water;

DOI:10.1016/S0040-4039(00)00628-6

Reference yield: 90.0%

(3aS,6aS)-2,2-dimethyl-3a-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (366462-72-8) → (-)-pentenomycin (49644-25-9,57236-37-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(01)01099-1

Reference yield: 84.0%

(2S,3S,4R)-2-hydroxymethyl-2,3,4-trihydroxycyclopentan-1-one (86531-78-4) → (-)-pentenomycin (49644-25-9,57236-37-0)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/S0040-4039(00)81578-6

upstream raw materials:

(2S,3S,4R)-2-hydroxymethyl-2,3,4-trihydroxycyclopentan-1-one

(2S,3S,4R)-3,4-dihydroxy-4-t-butyldimethylsilyloxy-2-t-butyldimethylsilyloxymethylcyclopentan-1-one

(3aS,6aS)-3a-Methoxymethoxymethyl-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

4,5,6-tri-O-acetylpentenomycin I

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