beta-D-Xylopyranosyl chloride, triacetate

Base Information

• Chemical Name: beta-D-Xylopyranosyl chloride, triacetate
• CAS No.: 10300-18-2
• Molecular Formula: C11H15 Cl O7
• Molecular Weight: 294.6856
• NSC Number: 109283,109282
• DSSTox Substance ID: DTXSID40296425
• Mol file: 10300-18-2.mol

Synonyms:10300-18-2;2,3,4-tri-o-acetylpentopyranosyl chloride;.beta.-D-Xylopyranosyl chloride, triacetate;.alpha.-D-Xylopyranosyl chloride, triacetate;10343-54-1;DTXSID40296425;Xylopyranosyl chloride, .beta.-D-;Xylopyranosyl chloride, .alpha.-D-;NSC109282;NSC109283;NSC-109282;NSC-109283;Tri-O-acetyl-.alpha.-D-xylopyranosyl chloride

Chemical Property of beta-D-Xylopyranosyl chloride, triacetate

Chemical Property:

• Vapor Pressure: 0.000162mmHg at 25°C
• Boiling Point: 330.8°Cat760mmHg
• Flash Point: 124.2°C
• Density: 1.32g/cm³
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 294.0506305
• Heavy Atom Count: 19
• Complexity: 370

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)Cl

Technology Process of beta-D-Xylopyranosyl chloride, triacetate

There total 8 articles about beta-D-Xylopyranosyl chloride, triacetate 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: 88.0%

tetra-O-acetyl-β-D-xylopyranose (4049-33-6) → (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl) chloride (10300-18-2)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In dichloromethane; for 0.0833333h;

DOI:10.1016/S0040-4039(02)02446-2

Reference yield:

α-D-xylopyranose tetraacetate (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0) → (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl) chloride (10300-18-2)

Guidance literature:

With titanium tetrachloride; In chloroform; at 70 ℃; for 3h;

DOI:10.1002/adsc.202100343

Reference yield:

3-(anthraquinon-1-yl)-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)triazene → 1-azidoanthracene-9,10-dione (42013-62-7) + (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl) chloride (10300-18-2) + 2,3,4-tri-O-acetyl-α-D-xylopyranosyl chloride (10343-54-1)

Guidance literature:

With tert-butylhypochlorite; In dichloromethane; at 0 ℃; for 1h; Title compound not separated from byproducts;

upstream raw materials:

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

tetra-O-acetyl-β-D-xylopyranose

1,2,3,4-tetra-O-acetyl-D-xylopyranose

aluminium trichloride

Downstream raw materials:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl chloride

α-D-xylopyranosyl azide

(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)benzene

1-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-4-retinamidobenzene

Refernces

• 1、 Mou, Ze-Dong,Wang, Jia-Xi,Zhang, Xia,Niu, Dawen. "Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides". supporting information. p. 3025 - 3029. Retrieved 2021/05/27.
• 2、 Weng, Min,Jochims, Johannes C.. "Preparation of glycosyltriazenes". . p. 530 - 536. Retrieved 2007/10/03.