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

• 1、 Xie,Berges,Robins. "Efficient 'dehomologation' of di-O-isopropylidenehexofuranose derivatives to give O-isopropylidenepentofuranoses by sequential treatment with periodic acid in ethyl acetate and sodium borohydride". . p. 5178 - 5179. Retrieved 1996.
• 2、 Swamy, N.Raghavendra,Venkateswarlu. "A mild and efficient method for chemoselective deprotection of acetonides by bismuth(III) trichloride". . p. 7549 - 7552. Retrieved 2002.
• 3、 McGuire, Thomas M.,Bowles, Jessica,Deane, Edward,Farrar, Elliot H. E.,Grayson, Matthew N.,Buchard, Antoine. "Control of Crystallinity and Stereocomplexation of Synthetic Carbohydrate Polymers from d- and l-Xylose". supporting information. p. 4524 - 4528. Retrieved 2021/01/12.
• 4、 Liu, Feng-Wu,Ji, Shujie,Gao, Yingying,Meng, Yao,Xu, Wenke,Wang, Haixia,Yang, Jing,Huang, Hao,Herdewijn, Piet,Wang, Cong. "Synthesis and in vitro antitumour activity of 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides". . . Retrieved 2021/05/19.