(3aR,6aR)-6-(benzyloxymethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Base Information

• Chemical Name: (3aR,6aR)-6-(benzyloxymethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one
• CAS No.: 89291-75-8
• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.317
• Mol file: 89291-75-8.mol

Synonyms:(3aR,6aR)-6-(benzyloxyMethyl)-2,2-diMethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Chemical Property of (3aR,6aR)-6-(benzyloxymethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Chemical Property:

• PSA: 44.76000
• LogP: 2.23240

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aR,6aR)-6-(benzyloxymethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

There total 45 articles about (3aR,6aR)-6-(benzyloxymethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-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: 84.0%

(4R,5S)-(-)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopenten-1-ol (328396-53-8) → (3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1246/cl.2004.506

Reference yield: 75.0%

(1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol (681853-99-6) → (3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/jo0356762

Reference yield: 59.0%

(1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol (681853-99-6) → (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone (1373332-57-0) + (3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Molecular sieve;

DOI:10.1021/jm3004009

upstream raw materials:

(3R,4R)-(-)-6-O-benzyl-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-erythro-2,5-hexodiulose

2,3-O-isopropylidene-D-ribonic-γ-lactone

benzyl bromide

(-)-6-O-benzyl-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-ribo-hexofuranose

Downstream raw materials:

(+/-)-6-O-Benzyl-3,4-O-isopropylidene-1,2-anhydro-2a,5-didehydro-2a-carba-α-psicofuranose

(+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose

(3aS,4S,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

(3aR,6S,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one