(3AR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3AR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 65025-94-7
• Molecular Formula: C₁₄H₂₆O₄Si
• Molecular Weight: 286.444
• UNII: 969U9P4EMK
• DSSTox Substance ID: DTXSID70442554
• Nikkaji Number: J1.378.894D
• Wikidata: Q82259890
• Mol file: 65025-94-7.mol

Synonyms:65025-94-7;(3aR,4S,5R,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;72777-85-6;(3AR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one;969U9P4EMK;SCHEMBL10989953;DTXSID70442554;(3aR,4S,5R,6aS)-4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one;(1S,5R,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one;(1R)-2beta-(tert-Butyldimethylsiloxymethyl)-3alpha,5alpha-dihydroxycyclopentane-1alpha-acetic acid 1,5-lactone;(3aR,4S,5R,6aS)-4-{[(tert-butyldimethylsilyl)oxy]methyl}-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one;2H-Cyclopenta[b]furan-2-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-hydroxy-, (3aR,4S,5R,6aS)-;2H-Cyclopenta[b]furan-2-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-hydroxy-, [3aR-(3aalpha,4alpha,5beta,6aalpha)]-

Chemical Property of (3AR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

• PSA: 55.76000
• LogP: 2.46320
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Chloroform (Slightly), Dichloromethane, DMSO (Slightly), Ethyl Acetate,
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 286.16003584
• Heavy Atom Count: 19
• Complexity: 361

Purity/Quality:

99.90% ^*data from raw suppliers

(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1C(CC2C1CC(=O)O2)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)O
• Uses: Intermediate in the preparation of prostaglandin derivatives

Technology Process of (3AR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

There total 20 articles about (3AR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-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: 97.0%

(3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-triethylsilanyloxy-hexahydro-cyclopenta[b]furan-2-one → (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (58707-50-9,72777-85-6,81203-78-3,65025-94-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In dichloromethane; at 20 ℃; for 0.0333333h; atmospheric pressure;

DOI:10.1016/j.tetlet.2003.12.145

Reference yield: 96.3%

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (58707-50-9,72777-85-6,81203-78-3,65025-94-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 10 ℃; for 2h;

Reference yield: 96.0%

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (65025-95-8) → (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (58707-50-9,72777-85-6,81203-78-3,65025-94-7)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; at -25 - 25 ℃; for 1h;

DOI:10.1016/S0040-4039(00)99965-9

upstream raw materials:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

Acetic acid (3aS,4R,5S,6aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Benzoic acid (1S,2R,3R,4R)-3-formyl-2-((Z)-oct-2-enyl)-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

(1S,2R,3S,4R)-1α-benzoyloxy-3β-hydroxymethyl-2α-(2Z-octenyl)-4α-(2-tetrahydropyranyloxy)-cyclopentane