1,2-O-Isopropylidene-alpha-D-xylofuranose

Base Information

• Chemical Name: 1,2-O-Isopropylidene-alpha-D-xylofuranose
• CAS No.: 20031-21-4
• Molecular Formula: C8H14O5
• Molecular Weight: 190.196
• Hs Code.: 29321900
• European Community (EC) Number: 606-426-9,922-380-5
• DSSTox Substance ID: DTXSID40885111
• Nikkaji Number: J119.581F
• Wikidata: Q72485991
• ChEMBL ID: CHEMBL499271
• Mol file: 20031-21-4.mol

Synonyms:1,2-O-isopropylidene-alpha-D-xylofuranose

Chemical Property of 1,2-O-Isopropylidene-alpha-D-xylofuranose

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 1E-05mmHg at 25°C
• Melting Point: 69-71 °C
• Refractive Index: -19 ° (C=1, H2O)
• Boiling Point: 333 °C at 760 mmHg
• PKA: 13.23±0.60(Predicted)
• Flash Point: 155.2 °C
• PSA: 68.15000
• Density: 1.267 g/cm³
• LogP: -0.78400
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 190.08412354
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98% ^*data from raw suppliers

1,2-O-Isopropylidene-α-D-xylofuranose ^*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(C(OC2O1)CO)O)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)CO)O)C
• Uses: 1,2-O-Isopropylidene-α-D-xylofuranose is an intermediate used in the synthesis of C-glycosides ribosyl-acid and ribosyl-aldehyde.

Technology Process of 1,2-O-Isopropylidene-alpha-D-xylofuranose

There total 54 articles about 1,2-O-Isopropylidene-alpha-D-xylofuranose 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%

1,2:3,5-di-O-isopropylidene-D-xylofuranose (20881-04-3) → 1,2-O-isopropylidene-α-D-xylose (20031-21-4)

Guidance literature:

With acetic acid; at 20 ℃; for 72h;

DOI:10.1016/S0040-4020(99)00959-X

Reference yield: 100.0%

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) → 1,2-O-isopropylidene-α-D-xylose (20031-21-4)

Guidance literature:

With sodium hydrogen sulfate; silica gel; In methanol; dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2004.07.075

Reference yield: 97.0%

D-xylose (58-86-6) + acetone (67-64-1) → 1,2-O-isopropylidene-α-D-xylose (20031-21-4)

Guidance literature:

D-xylose; acetone; With sulfuric acid;

With hydrogenchloride; In water;

DOI:10.1055/s-2008-1077953

upstream raw materials:

5-amino-5-deoxy-1,2-O-isopropylidene-a-D-xylofuranose

1,2:3,5-di-O-isopropylidene-D-xylofuranose

Butyric acid (3aR,5R,6S,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

benzoyl chloride

Downstream raw materials:

O¹,O²-isopropylidene-O³,O⁵-(4-nitro-phenoxyphosphoryl)-α-D-xylofuranose

D-xylose

5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

Refernces

Branched-chain thiosugars: Temperature effects in the acetolytic deacetalation of furanose sugars

10.1016/0008-6215(91)80095-5

The research focuses on the synthesis and acetolytic deacetalation of branched-chain thiosugar derivatives, specifically 8 and 13, derived from 1,2-O-isopropylidene-D-xylofuranose. The study investigates the effects of temperature on the reaction outcomes, revealing that lower temperatures lead to the formation of novel thiolanes (9 and 17) due to furanose ring opening, while higher temperatures yield the desired 1,2-di-O-acetyl furanoses (6 and 14). Key chemicals involved in the synthesis include p-toluenesulfonic acid (TsOH), acetic anhydride, lithium aluminium hydride, trichloroacetic acid, and tert-butyldiphenylsilyl chloride. The research also explores the use of boron trifluoride etherate and camphorsulfonic acid (CSA) as alternative catalysts, highlighting the significant role of reaction temperature in determining product distribution and the potential for ring-opening and ring-expansion pathways in the acetolysis of these thiosugars.

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