(3aS,6S,7aS)-6-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one

Base Information

• Chemical Name: (3aS,6S,7aS)-6-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one
• CAS No.: 4096-62-2
• Molecular Formula: C9H14O5
• Molecular Weight: 202.207
• DSSTox Substance ID: DTXSID10462271
• Nikkaji Number: J1.712.764K
• Wikidata: Q82286779
• Mol file: 4096-62-2.mol

Synonyms:4096-62-2;(3aS,6S,7aS)-6-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one;SCHEMBL7156154;DTXSID10462271;ZAKORQDMJYUIOY-GEVIPFJHSA-N;1-O-Methyl-3-O,4-O-isopropylidene-beta-L-erythro-2-pentulopyranose;L-erythro-Pentopyranosidulose, methyl 3,4-O-isopropylidene-, .beta.-;(3aS,6S,7aS)-6-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyran-7-one;.beta.-L-erythro-Pentopyranosid-2-ulose, methyl 3,4-O-(1-methylethylidene)-

Chemical Property of (3aS,6S,7aS)-6-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one

Chemical Property:

• PSA: 53.99000
• LogP: 0.07830
• Solubility.: Chloroform, Dichloromethane. Ethyl Acetate
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 202.08412354
• Heavy Atom Count: 14
• Complexity: 250

Purity/Quality:

97% ^*data from raw suppliers

Methyl3,4-O-Isopropylidene-β-L-erythro-pentopyranosid-2-ulose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2COC(C(=O)C2O1)OC)C
• Isomeric SMILES: CC1(O[C@H]2CO[C@@H](C(=O)[C@H]2O1)OC)C

Technology Process of (3aS,6S,7aS)-6-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one

There total 7 articles about (3aS,6S,7aS)-6-methoxy-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-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: 83.0%

methyl 3,4-O-isopropylidene-β-L-arabinopyranoside (6960-39-0,817620-70-5) → methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose (4096-62-2)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; acetic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(03)00145-5

Reference yield:

methyl β-L-arabinopyranoside (91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,14703-09-4,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5) → methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose (4096-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / p-TsOH / acetone / 20 °C

2: 83 percent / PDC; AcOH; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With dipyridinium dichromate; 4 A molecular sieve; toluene-4-sulfonic acid; acetic acid; In dichloromethane; acetone;

DOI:10.1016/S0040-4020(03)00145-5

Reference yield:

β-L-arabinopyranose (7296-56-2) → methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosid-2-ulose (4096-62-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / acetyl chloride / 7 h / Heating

2: 100 percent / sulfuric acid / acetone / 24 h / Ambient temperature

3: 23 percent / pyridinium chlorochromate, molecular sieves 3A / 3 h / Ambient temperature

With 3 A molecular sieve; sulfuric acid; acetyl chloride; pyridinium chlorochromate; In acetone;

DOI:10.1021/jf980506p

upstream raw materials:

methyl 3,4-O-isopropylidene-β-L-arabinopyranoside

L-(+)-arabinose

methyl β-L-arabinopyranoside

β-L-arabinopyranose

Downstream raw materials:

Methyl-3,4-O-isopropyliden-β-L-ribosid

2S-methoxytetrahydropyran-3,4-dione 4-phenylhydrazone

3,4-O-isopropylidene-L-erythro-pentosazone

methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosidulose syn-phenylhydrazone

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