(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one

Base Information

• Chemical Name: (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one
• CAS No.: 90529-18-3
• Molecular Formula: C₁₂H₁₆O₆
• Molecular Weight: 256.255

Synonyms:(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property of (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property:

Purity/Quality:

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Technology Process of (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one

There total 2 articles about (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one (90529-18-3) + (4aR,4bS,7aR,8aS)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one (80114-08-5,107796-40-7,109122-52-3,119008-00-3)

Guidance literature:

With sulfuric acid; acetic anhydride; In acetic acid; Yields of byproduct given. Title compound not separated from byproducts; 1) 70 to 80 deg C, 20 h, 2) 60 to 65 deg C,40 h; sealed vessel;

DOI:10.1016/S0040-4020(01)86203-7

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + acetic anhydride (108-24-7) + cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one (90529-18-3) + (4aR,4bS,7aR,8aS)-Hexahydro-furo[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6-one (80114-08-5,107796-40-7,109122-52-3,119008-00-3)

Guidance literature:

With sulfuric acid; In acetic acid; Yields of byproduct given. Title compound not separated from byproducts; 1) 70 to 80 deg C, 20 h, 2) 60 to 65 deg C,40 h; sealed vessel;

DOI:10.1016/S0040-4020(01)86203-7

Reference yield: 20.0%

(1SR, 5RS, 6RS, 7RS)-7-acetoxy-6-acetoxymethyl-2-oxabicyclo<3.3.0>octan-3-one (90529-18-3) → (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) + (1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one (26054-65-9) + <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) + (3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one (125226-81-5)

Guidance literature:

With sodium hydroxide; Soerensen phosphate buffer; In methanol; at 36 ℃; for 24h; Further byproducts given. Yields of byproduct given; subtilisin DY;

upstream raw materials:

formaldehyd

cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one

acetic anhydride

Downstream raw materials:

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

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one

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

(3aS,4R,5S,6aR)-5-acetoxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one

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