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

Base Information

• Chemical Name: (3aS,4R,5S,6aR)-5-(Benzyloxy)-4-((benzyloxy)methyl)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 114826-79-8
• Molecular Formula: C22H24O4
• Molecular Weight: 352.43
• DSSTox Substance ID: DTXSID10554029
• Wikidata: Q82434826
• Mol file: 114826-79-8.mol

Synonyms:114826-79-8;(3aS,4R,5S,6aR)-5-(Benzyloxy)-4-((benzyloxy)methyl)hexahydro-2H-cyclopenta[b]furan-2-one;(3aS,4R,5S,6aR)-5-phenylmethoxy-4-(phenylmethoxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;(3AS,4R,5S,6AR)-5-(BENZYLOXY)-4-((BENZYLOXY)METHYL)-HEXAHYDRO-2H-CYCLOPENTA[B]FURAN-2-ONE;(3aS,4R,5S,6aR)-5-(Benzyloxy)-4-[(benzyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one;SCHEMBL15198005;DTXSID10554029;J-501172;2H-Cyclopenta[b]furan-2-one, hexahydro-5-(phenylMethoxy)-4-[(phenylMethoxy)Methyl]-, [3aS-(3aa,4a,5b

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

Chemical Property:

• PSA: 44.76000
• LogP: 3.74020
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 352.16745924
• Heavy Atom Count: 26
• Complexity: 453

Purity/Quality:

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

(3AS,4R,5S,6aR)-5-(Benzyloxy)-4-((benzyloxy)methyl)-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: C1C2C(CC(=O)O2)C(C1OCC3=CC=CC=C3)COCC4=CC=CC=C4
• Isomeric SMILES: C1[C@@H]2[C@@H](CC(=O)O2)[C@@H]([C@H]1OCC3=CC=CC=C3)COCC4=CC=CC=C4

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

There total 2 articles about (3aS,4R,5S,6aR)-5-(Benzyloxy)-4-((benzyloxy)methyl)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: 71.6%

benzyl bromide (100-39-0) + <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) → (3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one (114826-79-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃;

Reference yield:

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) → (3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one (114826-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) H₂SO₄, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H⁺), 70 deg C, 15 h

2: 60 percent / NaH / dimethylformamide

With sulfuric acid; sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)91379-6

Reference yield: 92.1%

bromobenzene (108-86-1,52753-63-6) + (3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one (114826-79-8) → C34H36O4

Guidance literature:

bromobenzene; With iodine; magnesium; In diethyl ether; for 1h; Inert atmosphere;

(3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one; In diethyl ether; at -10 - 0 ℃; Inert atmosphere;

upstream raw materials:

benzyl bromide

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

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

Downstream raw materials:

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

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

(1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol

(1R, 3S, 4R)-1-amino-3-benzyloxy-4-(benzyloxymethyl)cyclopentane

Refernces

• 1、 -. "Preparation method of entecavir intermediate". Paragraph 0173-0176. . Retrieved 2019/02/06.