3-Cyclopentene-1,2-diol, 5-(hydroxymethylamino)-4-2-(phenylthio)ethenyl-, 1,2-diacetate, 1S-1.alpha.,2.beta.,4(E),5.beta.-

Base Information

• Chemical Name: 3-Cyclopentene-1,2-diol, 5-(hydroxymethylamino)-4-2-(phenylthio)ethenyl-, 1,2-diacetate, 1S-1.alpha.,2.beta.,4(E),5.beta.-
• CAS No.: 88111-93-7
• Molecular Formula: C₁₈H₂₁NO₅S
• Molecular Weight: 363.434
• Mol file: 88111-93-7.mol

Synonyms:3-Cyclopentene-1,2-diol, 5-(hydroxymethylamino)-4-2-(phenylthio)ethenyl-, 1,2-diacetate, 1S-1.alpha.,2.beta.,4(E),5.beta.-

Chemical Property of 3-Cyclopentene-1,2-diol, 5-(hydroxymethylamino)-4-2-(phenylthio)ethenyl-, 1,2-diacetate, 1S-1.alpha.,2.beta.,4(E),5.beta.-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Cyclopentene-1,2-diol, 5-(hydroxymethylamino)-4-2-(phenylthio)ethenyl-, 1,2-diacetate, 1S-1.alpha.,2.beta.,4(E),5.beta.-

There total 10 articles about 3-Cyclopentene-1,2-diol, 5-(hydroxymethylamino)-4-2-(phenylthio)ethenyl-, 1,2-diacetate, 1S-1.alpha.,2.beta.,4(E),5.beta.- 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: 24.0%

(phenylthiomethyl)triphenylphosphonium chloride + (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-4-exo-hydroxy-N-methyl-3-oxa-2-azabicyclo<3.3.0>octane (88111-88-0) → Z-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene (88111-93-7,88196-05-8) + E-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene (88111-93-7,88196-05-8)

Guidance literature:

With sodium methylsulfinylmethanide; In dimethyl sulfoxide; at 80 ℃; for 10h;

Reference yield: 24.0%

(phenylthiomethyl)triphenylphosphonium chloride + (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-4-exo-hydroxy-N-methyl-3-oxa-2-azabicyclo<3.3.0>octane (88111-88-0) → Z-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene (88111-93-7,88196-05-8) + E-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene (88111-93-7,88196-05-8)

Guidance literature:

With sodium methylsulfinylmethanide; In dimethyl sulfoxide; at 80 ℃; for 10h;

Reference yield:

Acetic acid (E)-(1S,2R)-2-acetoxy-1-((R)-1-acetoxy-2-oxo-ethyl)-4-phenylsulfanyl-but-3-enyl ester → Z-(3S,4S,5R)-3,4-diacetoxy-5-(N-hydroxy-N-methylamino)-1-<2-(phenylthio)vinyl>cyclopent-1-ene (88111-93-7,88196-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 16 percent / pyridine, N-methylhydroxylamine hydrochloride / ethanol / 0.5 h / 50 °C

2: mercury⁽¹¹⁾ acetate / acetone; H₂O / 0.33 h

3: 24 percent / dimsyl sodium / dimethylsulfoxide / 10 h / 80 °C

With pyridine; N-methylhydroxyamine hydrochloride; mercury(II) diacetate; sodium methylsulfinylmethanide; In ethanol; water; dimethyl sulfoxide; acetone;

upstream raw materials:

(1R,5S)-6-exo,7-endo,8-exo-triacetoxy-4-exo-hydroxy-N-methyl-3-oxa-2-azabicyclo<3.3.0>octane

(1R,5S)-6-exo,7-endo,8-exo-triacetoxy-N-methyl-4-exo-phenylthio-3-oxa-2-azabicyclo<3.3.0>octane

(1R,5S)-6-exo,7-endo,8-exo-triacetoxy-N-methyl-4-endo-phenylthio-3-oxa-2-azabicyclo<3.3.0>octane

(6R)-2,3,4,-tri-O-acetyl-1,6-anhydro-6-phenylthio-β-D-glucopyranose