2,3-O-Isopropylidene-1-O-methyl-D-ribosic acid

Base Information

• Chemical Name: 2,3-O-Isopropylidene-1-O-methyl-D-ribosic acid
• CAS No.: 54622-95-6
• Molecular Formula: C9H14O6
• Molecular Weight: 218.207
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID20448844
• Nikkaji Number: J1.884.725F
• Wikidata: Q82268020
• Mol file: 54622-95-6.mol

Synonyms:54622-95-6;2,3-O-Isopropylidene-1-O-methyl-D-ribosic acid;(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid;(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid;methyl 2,3-O-(1-methylethylidene)-beta-D-ribofuranosiduronic acid;ST092333;SCHEMBL6573945;DTXSID20448844;BTFKDZSYIKUCGF-BYPJNBLXSA-N;MFCD10039832;AKOS024286209;AS-19629;CS-0064750;C75561;2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSICACID;Methyl 2-O,3-O-isopropylidene-beta-D-ribofuranosiduronic acid;(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylicacid

Chemical Property of 2,3-O-Isopropylidene-1-O-methyl-D-ribosic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 129-130°C
• Refractive Index: 1.504
• Boiling Point: 341.604°C at 760 mmHg
• PKA: 2.67±0.60(Predicted)
• Flash Point: 135.064°C
• PSA: 74.22000
• Density: 1.341g/cm³
• LogP: -0.03760
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in methanol.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 218.07903816
• Heavy Atom Count: 15
• Complexity: 276

Purity/Quality:

98%, ^*data from raw suppliers

(3AS,6R,6AR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(O1)C(OC2C(=O)O)OC)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](O1)[C@@H](O[C@@H]2C(=O)O)OC)C

Technology Process of 2,3-O-Isopropylidene-1-O-methyl-D-ribosic acid

There total 4 articles about 2,3-O-Isopropylidene-1-O-methyl-D-ribosic acid 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%

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (54622-95-6)

Guidance literature:

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol; With sodium hypochlorite; tetrabutylammomium bromide; sodium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; In dichloromethane; at 0 - 20 ℃; for 1h;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; Further stages.;

DOI:10.1002/chem.200600290

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (54622-95-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HClO₄ / acetone / 2.5 h / 20 °C

2: aq. HClO₄ / acetone / 2 h / 20 °C

3: aq. NaHCO₃; NaClO; TEMPO / KBr / ethyl acetate / 3 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; perchloric acid; sodium hydrogencarbonate; potassium bromide; In ethyl acetate; acetone;

DOI:10.1021/jm031143+

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (54622-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HClO₄ / acetone / 2 h / 20 °C

2: aq. NaHCO₃; NaClO; TEMPO / KBr / ethyl acetate / 3 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; perchloric acid; sodium hydrogencarbonate; potassium bromide; In ethyl acetate; acetone;

DOI:10.1021/jm031143+

upstream raw materials:

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

2,3-O-isopropylidene-D-ribofuranose

D-Ribose

Downstream raw materials:

(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate

(2S,3R)-2-(Benzhydryl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-((3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester

methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate