<3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one

Base Information

• Chemical Name: <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one
• CAS No.: 134875-85-7
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.278
• Mol file: 134875-85-7.mol

Synonyms:<3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one

Chemical Property of <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one

There total 12 articles about <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-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: 91.5%

(+/-)-4S-<(benzyloxy)methyl>-1-<(4'-methylphenyl)sulfonyl>cyclopent-5-eno<4,5-d>-3aR,6aS-1,3-oxazolidinone (124583-65-9,143729-91-3,143729-95-7) → (+/-)-4S-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-3aR,6aS-oxazolidin-2-one (124583-62-6,134875-85-7)

Guidance literature:

With naphthalene; sodium; In 1,2-dimethoxyethane; at -78 ℃;

Reference yield: 63.0%

<1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate (134756-65-3) → <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one (134875-85-7)

Guidance literature:

With triethylamine; trifluoroacetic acid; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ja00015a051

Reference yield: 35.0%

(1R,2S)-2-(benzyloxymethyl)cyclopent-3-enyl carbamate (1159996-26-5) → C14H15NO3 (1159996-29-8) + C14H15NO3 + <3a(R)-(3aα,6α,6aα)>-6-<(benzyloxy)methyl>-3,3a,6,6a-tetrahydro-2H-cyclopentoxazol-2-one (134875-85-7)

Guidance literature:

(1R,2S)-2-(benzyloxymethyl)cyclopent-3-enyl carbamate; With 2,6-dimethylpyridine; [bis(acetoxy)iodo]benzene; In 1,2-dichloro-ethane; at 20 ℃; for 6h; Inert atmosphere;

With rhodium(II) acetate dimer; In 1,2-dichloro-ethane; at 40 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.03.092

upstream raw materials:

(+/-)-4S-<(benzyloxy)methyl>-1-<(4'-methylphenyl)sulfonyl>cyclopent-5-eno<4,5-d>-3aR,6aS-1,3-oxazolidinone

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

5-(benzyloxymethyl)cyclopentadiene

<1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate

Downstream raw materials:

(+/-)-4S-<(benzyloxy)methyl>-2-(N,N-dimethylamino)cyclopent-5-eno<4,5-d>-3aS,6aR-oxzoline

((1bR,4aR,5R)-5-Benzyloxymethyl-1b,4a,5,5a-tetrahydro-1aH-1,4-dioxa-2-aza-cyclopropa[a]pentalen-3-yl)-dimethyl-amine

(+/-)-allosamizoline

(+/-)-3aS,6aS-dihydro-5R,6S-dihydroxy-2-(dimethylamino)-4S-(hydroxymethyl)cyclopentano<4,3-d>oxazole