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

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• CAS No.: 57930-46-8
• Molecular Formula: C10H14O5
• Molecular Weight: 214.218
• Mol file: 57930-46-8.mol

Synonyms:6,6-dimethyl-2-oxobicyclo[3.1.11.5]heptane;(1S,5R)-2-(tert-butoxycarbonyl)-6-oxa-2-azabicyclo<3.2.1>octan-7-one;(1S,5R)-N-tert-butoxycarbonyl-6-oxa-7-oxo-2-azabicyclo[3.2.1]octane;(1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one;6,6-dimethylnorpinan-2-one;(1R)-()-Nopinone;(1S,5R)-6,6-dimethylbicyclo[3.1.1]heptan-2-one;(1S,5R)-(+)-nopinone;(1S,5R)-6,6-dimethylnorpinan-2-one;(1R,5S)-(+)-nopinone;

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

Chemical Property:

• Boiling Point: 383℃
• Flash Point: 153℃
• PSA: 72.83000
• Density: 1.297
• LogP: -0.13800

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 5 articles about (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-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: 70.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one (26054-65-9) + (1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (57930-46-8) + (4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one (109122-52-3) + (3aR,4S,5R,6aS)-5-(acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one (62939-82-6)

Guidance literature:

With sulfuric acid; acetic acid; at 75 - 80 ℃; for 24h;

DOI:10.1016/S0040-4020(01)88339-3

Reference yield: 70.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) + acetic acid (64-19-7,77671-22-8) → (1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one (26054-65-9) + (1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (57930-46-8) + (4aS,4bR,7aS,8aR)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one (109122-52-3) + (3aR,4S,5R,6aS)-5-(acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one (62939-82-6)

Guidance literature:

With sulfuric acid; at 75 - 80 ℃; for 24h;

DOI:10.1016/S0040-4020(01)88339-3

Reference yield: 47.4%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one (54423-47-1) → <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) + (1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (57930-46-8)

Guidance literature:

In dichloromethane; for 3h; Ambient temperature; lipase AK;

DOI:10.1248/cpb.39.2758

upstream raw materials:

formaldehyd

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

vinyl acetate

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

Downstream raw materials:

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

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