2-O,3-O-Isopropylidene-beta-D-threo-pentulofuranose

Base Information

• Chemical Name: 2-O,3-O-Isopropylidene-beta-D-threo-pentulofuranose
• CAS No.: 25018-68-2
• Molecular Formula: C₈H₁₄O₅
• Molecular Weight: 190.19
• DSSTox Substance ID: DTXSID401202853
• Nikkaji Number: J342.267D
• Mol file: 25018-68-2.mol

Synonyms:25018-68-2;SCHEMBL7147463;DTXSID401202853;2-O,3-O-Isopropylidene-beta-D-threo-pentulofuranose;beta-D-threo-2-Pentulofuranose, 2,3-O-(1-methylethylidene)-

Chemical Property of 2-O,3-O-Isopropylidene-beta-D-threo-pentulofuranose

Chemical Property:

• Boiling Point: 322.7±37.0 °C(Predicted)
• PKA: 13.30±0.60(Predicted)
• Density: 1.313±0.06 g/cm3(Predicted)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 190.08412354
• Heavy Atom Count: 13
• Complexity: 217

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(COC2(O1)CO)O)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](CO[C@]2(O1)CO)O)C

Technology Process of 2-O,3-O-Isopropylidene-beta-D-threo-pentulofuranose

There total 1 articles about 2-O,3-O-Isopropylidene-beta-D-threo-pentulofuranose 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:

ribulose (7558-89-6) + acetone (67-64-1) → DL-erythro-[2]pentulose (488-84-6,527-50-4,551-84-8,2042-27-5,5556-48-9,5962-29-8,7558-89-6,25577-44-0,83946-43-4) + 2,3-O-isopropylidene-β-DL-threo-2-pentulofuranose (25018-68-2,37106-13-1,117596-33-5)

Guidance literature:

With sulfuric acid; for 1.5h; Yield given. Title compound not separated from byproducts; Ambient temperature;

Reference yield: 45.0%

2,3-O-isopropylidene-β-D-threo-2-pentulofuranose (25018-68-2) + 4-methoxy-benzaldehyde (123-11-5) → (3aS,6R,6aS)-3a-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (204650-72-6)

Guidance literature:

With boron trifluoride;

DOI:10.1016/0040-4039(96)00611-9

Reference yield:

2,3-O-isopropylidene-β-D-threo-2-pentulofuranose (25018-68-2) → 3-Oxo-decanoic acid (3aS,6R,6aS)-3a-hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / BF₃

2: 21 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 6 h / Heating

With boron trifluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00611-9

upstream raw materials:

ribulose

acetone

Downstream raw materials:

(3aS,6R,6aS)-3a-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

((3aS,6R,6aS)-6-Benzyloxy-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-3a-yl)-methanol

3-Oxo-octanoic acid (3aS,6R,6aS)-6-benzyloxy-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-3a-ylmethyl ester

3-Oxo-decanoic acid (3S,4R)-3,4,5-trihydroxy-2-oxo-pentyl ester