(3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 92596-29-7
• Molecular Formula: C29H38O5Si
• Molecular Weight: 494.703
• DSSTox Substance ID: DTXSID70562908
• Mol file: 92596-29-7.mol

Synonyms:92596-29-7;(3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(oxan-2-yloxy)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;SCHEMBL957966;DTXSID70562908;(3aR,4S,5R,6aS)-4-({[tert-Butyl(diphenyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property of (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

• Boiling Point: 584.0±50.0 °C(Predicted)
• PSA: 53.99000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 4.42640
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 494.24885084
• Heavy Atom Count: 35
• Complexity: 690

Purity/Quality:

97% ^*data from raw suppliers

(3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-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](C1=CC=CC=C1)(C2=CC=CC=C2)OCC3C(CC4C3CC(=O)O4)OC5CCCCO5
• Isomeric SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC[C@H]3[C@@H](C[C@H]4[C@@H]3CC(=O)O4)OC5CCCCO5

Technology Process of (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[b]furan-2-one

There total 1 articles about (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-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:

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (3aR,4S,5R,6aS)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one (92596-29-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

Reference yield:

(3aR,4S,5R,6aS)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one (92596-29-7) → (3aR,4S,5R,6aS)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;

DOI:10.1021/acsmedchemlett.5b00455

Reference yield:

(3aR,4S,5R,6aS)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one (92596-29-7) → (4aR,5S,6R,7aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)octahydrocyclopenta[b]pyran-2,6-diyl diacetate

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

2.2: 0.5 h / 0 °C

3.1: acetic acid; water / tetrahydrofuran / 3 h / 55 °C

4.1: pyridine / 14 h / 0 - 20 °C

With pyridine; potassium tert-butylate; water; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; toluene;

DOI:10.1021/acsmedchemlett.5b00455

upstream raw materials:

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one

tert-butylchlorodiphenylsilane

Downstream raw materials:

(Z)-7-[(1R,2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methylene-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

isocarbacyclin

5-[(3aS,5R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(tetrahydro-pyran-2-yloxy)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester

5-[(1bS,3R,4S,4aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(tetrahydro-pyran-2-yloxy)-hexahydro-1-oxa-cyclopropa[a]pentalen-5a-yl]-pentanoic acid methyl ester