(3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate

Base Information

• Chemical Name: (3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate
• CAS No.: 14440-57-4
• Molecular Formula: C₁₄H₂₂O₇
• Molecular Weight: 302.324
• Nikkaji Number: J1.255.414A
• Mol file: 14440-57-4.mol

Synonyms:(3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate

Chemical Property of (3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate

Chemical Property:

• Vapor Pressure: 2.62E-05mmHg at 25°C
• Boiling Point: 358°C at 760 mmHg
• Flash Point: 155.1°C
• Density: 1.25g/cm³
• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2C(C(O1)C3COC(O3)(C)C)OC(O2)(C)C
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H]2[C@H]([C@H](O1)[C@H]3COC(O3)(C)C)OC(O2)(C)C

Technology Process of (3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl acetate

There total 8 articles about (3aS,4R,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-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: 96.0%

acetic anhydride (108-24-7) + 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14131-84-1) → 1-O-acetyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14440-57-4)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.202110391

Reference yield: 86.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + 3,6-anhydro-1,2:4,5-di-O-isopropylidene-D-glycero-D-manno-heptitol (144651-34-3,144732-47-8) → 1-O-acetyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14440-57-4) + (1R,2R,6R,7R)-7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,4-dimethyl-3,5,8,10-tetraoxa-tricyclo[5.2.1.02,6]decane

Guidance literature:

With iodine; In dichloromethane; at 20 ℃; for 1.5h; Irradiation;

DOI:10.1021/jo026004z

Reference yield:

D-Mannose (3458-28-4) → 1-O-acetyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14440-57-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄ / H₂O / 1 h / 20 °C

2: ethyl acetate / 0.5 h / 60 °C

With sulfuric acid; In water; ethyl acetate; 1: Cyclization / 2: Acetylation;

DOI:10.1021/ac990724x

upstream raw materials:

acetic acid

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

diisopropyl-carbodiimide

2,3,5,6-di-O-isopropylidene-D-mannofuranose

Downstream raw materials:

1-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylthioureido)-β-L-gulofuranose

1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

1-O-acetyl-2,3-O-isopropylidene-6-O-trityl-α-D-mannofuranose

1-O-acetyl-5-azido-5-deoxy-2,3-O-isopropylidene-6-O-trityl-β-L-gulofuranose