[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate

Base Information

• Chemical Name: [(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS No.: 16713-80-7
• Molecular Formula: C14H22 O7
• Molecular Weight: 302.32
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID701030906
• Mol file: 16713-80-7.mol

Synonyms:DTXSID701030906;AKOS024306913;CCG-252177

Chemical Property of [(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate

Chemical Property:

• Appearance/Colour: White crystalline solid
• Melting Point: 60-62 °C(lit.)
• Refractive Index: 1.6380 (estimate)
• Boiling Point: 333.3°Cat760mmHg
• Flash Point: 147.5°C
• PSA: 72.45000
• Density: 1.4g/cm³
• LogP: 0.94600
• Storage Temp.: 0-6°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 302.13655304
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

98%min ^*data from raw suppliers

3-O-Acetyl-1,2:5,6-di-O-isopropylidene-a-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(OC2C1OC(O2)(C)C)C3COC(O3)(C)C
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H]2[C@H](O[C@@H]1C3COC(O3)(C)C)OC(O2)(C)C

Technology Process of [(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate

There total 22 articles about [(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate 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: 98.0%

acetic anhydride (108-24-7) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200500555

Reference yield: 98.0%

acetyl chloride (75-36-5) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2005.11.035

Reference yield: 75.0%

acetic anhydride (108-24-7) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 6-O-acetyl-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose (36792-04-8) + 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7)

Guidance literature:

With vanadyl triflate; In dichloromethane; at -5 ℃; for 49h;

DOI:10.1021/ol016684c

upstream raw materials:

acetic anhydride

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt

acetyl chloride

N,N-dimethyl acetamide

Downstream raw materials:

(R)-3-hydroxy-3-phenylbutyric acid methyl ester

(-)S β-hydroxy β-phenyl n-butanoate de methyle

3-O-acetyl-6-O-benzoyl-1,2-O-isopropylidene-5-O-methylsulphonyl-α-D-glucofuranose

2,2-dimethyl-4-phenyl-1,3-dioxolane

Refernces

• 1、 Dasgupta, Falguni,Hay, George W.,Szarek, Walter A.,Shilling, Wilbur L.. "Acetylation of carbohydrates by transesterification using ethyl acetate and sodium hydride". . p. 153 - 157. Retrieved 1983.
• 2、 Chapman, Robert S.L.,Francis, Molly,Lawrence, Ruth,Tibbetts, Joshua D.,Bull, Steven D.. "Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols". . p. 6442 - 6452. Retrieved 2018/10/02.
• 3、 Kim, Myong Jung,Chun, Moon Woo. "Synthesis of a novel bicyclic nucleoside with a 3,7-anhydrooctofuranosyl skeleton". . p. 291 - 295. Retrieved 2008/02/11.