5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose

Base Information

• Chemical Name: 5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose
• CAS No.: 53167-11-6
• Molecular Formula: C8H12 O5
• Molecular Weight: 188.18
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID60452541
• Nikkaji Number: J2.120.217G
• Wikidata: Q82273244
• Mol file: 53167-11-6.mol

Synonyms:53167-11-6;5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose;(3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde;1,2-O-ISOPROPYLIDENE-alpha-D-XYLO-PENTODIALDO-1,4-FURANOSE;SCHEMBL6212057;DTXSID60452541;RSHCFFAQYBYYGI-XZBKPIIZSA-N;AKOS006288257;CS-0453314;1-O,2-O-Isopropylidene-5-oxo-5-deoxy-alpha-D-xylofuranose;(3AR,5S,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

Chemical Property of 5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose

Chemical Property:

• PSA: 64.99000
• LogP: -0.57740
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

98%Min ^*data from raw suppliers

5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C=O)O)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)C=O)O)C
• Uses: 1,2-O-Isopropylidene-alpha-D-xylo-pentodialdo-1,4-furanose was investigated as a possible reagent in the intramolecular cyclization of alkoxyamino-sugars in preparation of glycosidase inhibitors.

Technology Process of 5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose

There total 12 articles about 5-Aldo-1,2-O-isopropylidene-a-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-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (53167-11-6)

Guidance literature:

With sodium periodate; In methanol; water; at 0 ℃; for 1h;

DOI:10.1039/c6ra10456h

Reference yield: 61.0%

1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose (253328-56-2) → 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (53167-11-6)

Guidance literature:

With sodium periodate; sodium hydrogencarbonate; In methanol; water; at 0 ℃;

DOI:10.1039/c2ob25213a

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (53167-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / aq. H₂SO₄ / methanol / 12 h

2: NaIO₄; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

With sodium periodate; sulfuric acid; sodium hydrogencarbonate; In methanol; dichloromethane;

DOI:10.1081/SCC-120017195

upstream raw materials:

1,2-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-α-D-xylose

lead(IV) tetraacetate

benzene

Downstream raw materials:

O¹,O²-isopropylidene-α-D-xylo-pentodiald-1,4-ose-5-phenylhydrazone

(3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

(3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol

(5R)-1,2-O-isopropylidene-5-C-(4-chlorophenyl)-α-D-xylofuranose

Refernces

• 1、 Schaffer,Isbell. "-". . p. 3864. Retrieved 1957.
• 2、 Dávila García, álvaro,Bernès, Sylvain,Sartillo-Piscil, Fernando,Meza-León, Rosa Luisa. "Synthesis of a truncated tetradenolide". . p. 4373 - 4379. Retrieved 2020.
• 3、 Kova?evi?, Ivana,Kesi?, Jelena,Popsavin, Mirjana,Francuz, Jovana,Koji?, Vesna,Jakimov, Dimitar,Rodi?, Marko V.,Zelenovi?, Bojana Sre?o,Benedekovi?, Goran,Popsavin, Velimir. "Asymmetric synthesis and biological evaluation of (+)-cardiobutanolide, (?)-3-deoxycardiobutanolide and analogues as antiproliferative agents". supporting information. . Retrieved 2021/08/30.
• 4、 Kalmode, Hanuman P.,Maity, Dilip K.,Bhate, Prakash M.. "Thermal and Lewis acid promoted intramolecular Diels-Alder reaction of furanose tethered 1,3,9-decatriene systems: A synthetic and computational investigation". . p. 63445 - 63462. Retrieved 2016/07/19.