(3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 65025-95-8
• Molecular Formula: C19H34 O5 Si
• Molecular Weight: 370.561
• DSSTox Substance ID: DTXSID60517568
• Mol file: 65025-95-8.mol

Synonyms:65025-95-8;(3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(oxan-2-yloxy)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[b]furan-2-one;CID 13080724;4-(T-BUTYLDI-ME-SIO-ME)HEXA-H-5-(T-H-PYR AN -2-YLOXY)-CYCLOPENTA(B)FURAN-2-ON, 97;JJMNYDDYIZNLIX-GRDYTRHSSA-N;SCHEMBL3443781;DTXSID60517568;(3aR,4S,5R,6aS)-4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one;[3aR-(3a|A,4|A,5|A,6a|A)]-4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one;J-501162;(3aR,4S,5R,6aS) -4-(t-butyldimethylsilyloxymethyl)-5-(2-tetrahydropyranyloxy)hexahydrocyclopenta[b]furan-2-one;(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)-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)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-tetrahydropyranyloxy-hexahydro-2H-cyclopenta[

Chemical Property of (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

• Melting Point: 40-53 °C(lit.)
• Refractive Index: 1.488
• Flash Point: 113ºC
• PSA: 53.99000
• Density: 1.07g/cm3
• LogP: 3.87160
• Storage Temp.: 2-8°C
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 370.21755072
• Heavy Atom Count: 25
• Complexity: 487

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)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](C)(C)OCC1C(CC2C1CC(=O)O2)OC3CCCCO3
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)OC3CCCCO3
• Uses: Intermediate in the preparation of prostaglandin derivatives

Technology Process of (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one

There total 15 articles about (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)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: 100.0%

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

DOI:10.1021/acsmedchemlett.6b00415

Reference yield: 98.0%

3,4-dihydro-2H-pyran (110-87-2) + (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) → (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)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.03.069

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / 24 h / 50 - 80 °C / Sealed tube

2.1: DBN / methanol / 12 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

3.2: 8 h / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With 1H-imidazole; sulfuric acid; DBN; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.03.069

upstream raw materials:

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

tert-butyldimethylsilyl chloride

3,4-dihydro-2H-pyran

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

Downstream raw materials:

(3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

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

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

(1S,5R,6S,7R)-7-(tetrahydropyran-2-yl)oxy-6-(tetrahydropyran-2-yl)oxymethyl-2-oxabicyclo[3.3.0]octan-3-one

Refernces

• 1、 -. "The preparation method of the ruby's forefront". Paragraph 0035-0036. . Retrieved 2018/04/01.
• 2、 -. "Before preparing a Lima intermediate row element, method for preparing the same and before the Lima row element through its method of preparation". Paragraph 0069 - 0071. . Retrieved 2017/03/23.