(2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Base Information

• Chemical Name: (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
• CAS No.: 191528-77-5
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268

Synonyms:(2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Chemical Property of (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

There total 5 articles about (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 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: 94.0%

(2R,3aR,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-one (191528-76-4) → (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (191528-77-5)

Guidance literature:

With sodium tetrahydroborate; acetic acid; In benzene; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00387-6

Reference yield:

2,3-O-(R)-benzylidene-D-ribono-1,4-lactone → (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (191528-77-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaOH, 2.) NaIO₄ / 1.) H₂O, 45 deg C, 30 min, 2.) 0 deg C, 45 min

2: 94 percent / PPTS / CH₂Cl₂ / 5 h

3: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 45 min

4: 55 percent / benzophenone / 1.5 h / Irradiation

5: 94 percent / hlacial AcOH, NaBH₄ / benzene / 48 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; benzophenone; pyridinium p-toluenesulfonate; acetic acid; In dichloromethane; benzene;

DOI:10.1016/S0040-4020(97)00387-6

Reference yield:

(2R,3R)-O-benzylidene-2,3-dihydroxycyclopent-4-enone (191528-75-3) → (2R,3aS,4S,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol (191528-77-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / benzophenone / 1.5 h / Irradiation

2: 94 percent / hlacial AcOH, NaBH₄ / benzene / 48 h / Ambient temperature

With sodium tetrahydroborate; benzophenone; acetic acid; In benzene;

DOI:10.1016/S0040-4020(97)00387-6

upstream raw materials:

(2R,3aR,6R,6aR)-6-Hydroxymethyl-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

(2R,3R)-O-benzylidene-2,3-dihydroxycyclopent-4-enone

(2R,3aR,6S,6aS)-6-Hydroxy-2-phenyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

(2R,3aR,6S,6aS)-2-Phenyl-6-(tetrahydro-pyran-2-yloxy)-dihydro-furo[3,4-d][1,3]dioxol-4-one

Downstream raw materials:

Phosphoric acid (2R,3aR,4R,6S,6aS)-6-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester diphenyl ester

Morpholin-4-yl-phosphonic acid 2-cyano-ethyl ester (2R,3aR,4S,6R,6aR)-6-(diphenoxy-phosphoryloxymethyl)-2-phenyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

C₃₂H₃₆N₂O₉P₂

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