(3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Base Information

• Chemical Name: (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
• CAS No.: 30725-00-9
• Molecular Formula: C8H12 O5
• Molecular Weight: 188.18
• Hs Code.: 29322090
• European Community (EC) Number: 608-517-9
• DSSTox Substance ID: DTXSID101290883
• Nikkaji Number: J970.017J
• Mol file: 30725-00-9.mol

Synonyms:30725-00-9;(3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one;2,3-O-Isopropylidene-D-ribonic gamma-lactone;2,3-O-Isopropylidene-D-ribono-1,4-lactone;2,3-Isopropylidene-D-ribono-1,4-lactone;(3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one;D-Ribonic acid, 2,3-O-(1-methylethylidene)-, gamma-lactone;2,3-Isopropylidene-D-ribonolactone;MFCD00080793;2,3-O-Isopropylidene-D-ribonic acid-1,4-lactone;SCHEMBL2427628;NHHKFJCWLPPNCN-HSUXUTPPSA-;DTXSID101290883;CS-M1134;2,3-o-isopropylidene-d-ribonolactone;AKOS016843005;AC-32438;AS-10202;2,3-O-Isopropylidene-D-ribonic fA-Lactone;I1039;2,3-O-Isopropylidene-D-ribonic-gamma-lactone;EN300-219486;F12787;2-O,3-O-Isopropylidene-D-ribonic acid 1,4-lactone;W-202269;2,3-O-ISOPROPYLIDENE-D-RIBONIC GAMMA-LACTONE, 99%;(3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one

Chemical Property of (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 135-139 °C
• Refractive Index: 1.468
• Boiling Point: 338.1 °C at 760 mmHg
• PKA: 13.68±0.10(Predicted)
• Flash Point: 139.7 °C
• PSA: 64.99000
• Density: 1.258g/cm³
• LogP: -0.57580
• Storage Temp.: Refrigerator
• Solubility.: Soluble in methanol at 50mg/ml, acetone, dichloromethane, ethyl
• Water Solubility.: soluble
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

99.3% ^*data from raw suppliers

2,3-O-Isopropylidene-D-ribonic acid-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OC2C(OC(=O)C2O1)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](OC(=O)[C@@H]2O1)CO)C
• Description: 2,3-Isopropylidene-D-ribonolactone is a building block. It has been used in the stereocontrolled synthesis of the carbohydrates 6-epi-trehazolin and 6-epi-trehalamine.
• Uses: 2,3-O-Isopropylidene-D-ribonic acid-1,4-lactone is used for the synthesis of C-nucleosides, prostanoids and GABA analogs via homochiral 2-piperidones. It is the starting material for the preparation of biochemical compounds including C-nucleosides, such as neplanocin A, and GABA analogs, via homochiral 2-piperidones.

Technology Process of (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

There total 30 articles about (3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-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: 100.0%

2,2-dimethoxy-propane (77-76-9) + D-Ribono-1,4-lactone (5336-08-3) → 2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9)

Guidance literature:

With hydrogen cation; In acetone;

DOI:10.1246/cl.1985.1715

Reference yield: 100.0%

acetone (67-64-1) + D-Ribono-1,4-lactone (5336-08-3) → 2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9)

Guidance literature:

With sulfuric acid;

DOI:10.1080/15257770701542165

Reference yield: 99.0%

(3aR,6R,6aR)-6-(1-Benzyloxy-1-methyl-ethoxymethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one (89538-91-0) → 2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr; Ambient temperature;

DOI:10.1246/cl.1984.265

upstream raw materials:

D-Ribono-1,4-lactone

5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

(3aR,6R,6aR)-6-(1-Benzyloxy-1-methyl-ethoxymethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

(3aR,6R,6aR)-6-(1-Benzyloxy-2-fluoro-1-methyl-ethoxymethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

Downstream raw materials:

2,3-O-Isopropylidene-5-O-(p-tolylsulfonyl)-D-ribono-1,4-lactone

1-(1-benzyl-1H-benzoimidazol-2-yl)-O²,O³-isopropylidene-D-ribo-[1]pentulose

5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

(S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-(2-nitro-benzenesulfonyl)-amino]-4-methyl-pentanoic acid methyl ester