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

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-(Hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 69222-61-3
• Molecular Formula: C13H20 O5
• Molecular Weight: 256.299
• European Community (EC) Number: 614-936-8
• DSSTox Substance ID: DTXSID80509445
• Nikkaji Number: J28.191C
• Mol file: 69222-61-3.mol

Synonyms:69222-61-3;Corey lactone THP;(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(oxan-2-yloxy)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;2H-Cyclopenta[b]furan-2-one, hexahydro-4-(hydroxymethyl)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-, (3aR,4S,5R,6aS)-;SCHEMBL3710880;DTXSID80509445;CORRAXPZMWTYIP-TWEVDUBQSA-N;AKOS015995304;AKOS016009672;(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one;CS-0003841;A854985;J-501169;(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)-hexahydrocyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H -cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,5R,6AS)-4-(hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one

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

Chemical Property:

• Appearance/Colour: Colorless or light yellow viscous liquid
• Boiling Point: 454.2±45.0 °C(Predicted)
• PKA: 14.79±0.10(Predicted)
• PSA: 64.99000
• Density: 1.26
• LogP: 0.84210
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 256.13107373
• Heavy Atom Count: 18
• Complexity: 319

Purity/Quality:

98%, ^*data from raw suppliers

(3AR,4S,5R,6aS)-4-(Hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(C1)OC2CC3C(C2CO)CC(=O)O3
• Isomeric SMILES: C1CCOC(C1)O[C@@H]2C[C@H]3[C@@H]([C@H]2CO)CC(=O)O3
• Uses: (3aR,4S,5R,6aS)-hexahydro-4-(hydroxymethyl)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-Cyclopenta[b]furan-2-one belongs to furan heterocyclic derivatives and can be used as pharmaceutical intermediates in medical experimental research.

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

There total 20 articles about (3aR,4S,5R,6aS)-4-(Hydroxymethyl)-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: 94.6%

(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) → 2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

Reference yield: 93.4%

C21H27ClO6 → 2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3)

Guidance literature:

C₂₁H₂₇ClO₆; With water; sodium hydroxide; In methanol;

Acidic conditions;

Reference yield: 83.5%

C21H26ClNO8 → 2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3)

Guidance literature:

C₂₁H₂₆ClNO₈; With water; sodium hydroxide; In methanol;

Acidic conditions;

upstream raw materials:

3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde

3,4-dihydro-2H-pyran

5-oxo-1-cyclopenten-1-acetic acid methyl ester

Downstream raw materials:

(5aR,6S,7R,8aS)-6-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-3-[4-oxo-4-(2-propanyloxy)butyl]octahydro-2H-cyclopenta[b]oxepin-7-yl 4-biphenylcarboxylate

(3S,5aR,6S,7R,8aS)-6-(hydroxymethyl)-3-[4-oxo-4-(2-propanyloxy)butyl]octahydro-2H-cyclopenta[b]oxepin-7-yl 4-biphenylcarboxylate

(3S,5aR,6S,7R,8aS)-6-[(E)-2-iodovinyl]-3-[4-oxo-4-(2-propanyloxy)butyl]octahydro-2H-cyclopenta[b]oxepin-7-yl 4-biphenylcarboxylate

(3S,5aR,6R,7R,8aS)-6-[(1E)-3-hydroxy-5-(3-pyridinyl)-1-penten-1-yl]-3-[4-oxo-4-(2-propanyloxy)butyl]octahydro-2H-cyclopenta[b]oxepin-7-yl 4-biphenylcarboxylate

Refernces

• 1、 T?nase, Constantin I.,Dr?ghici, Constantin. "Transformation of δ-lactone in γ-lactone in the Corey route for synthesis of prostaglandins". . p. 845 - 853. Retrieved 2015/06/30.
• 2、 Miyaji, Katsuaki,Ohara, Yoshio,Takahashi, Yasuhiro,Tsuruda, Toshihiko,Arai, Kazutaka. "Synthesis of corey lactone via highly stereoselective asymmetric diels-alder reaction". . p. 4557 - 4560. Retrieved 2007/10/02.