TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE

Base Information

• Chemical Name: TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE
• CAS No.: 52443-06-8
• Molecular Formula: C12H15NO7
• Molecular Weight: 285.254
• Mol file: 52443-06-8.mol

Synonyms:TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE

Chemical Property of TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE

Chemical Property:

• PSA: 111.92000
• LogP: -0.29612

Purity/Quality:

97% ^*data from raw suppliers

TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE

There total 8 articles about TRI-O-ACETYL-D-XYLOPYRANOSYL CYANIDE 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: 89.0%

(E)-3,4,5-tri-O-acetyl-2,6-anhydro-D-gulose oxime acetate → 1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-xylopyranosyl cyanide (52443-06-8)

Guidance literature:

With sodium acetate; In acetic acid; at 100 ℃;

DOI:10.1080/07328300008544067

Reference yield: 84.0%

2,3,4-tri-O-acetyl-β-D-xylopyranosyl(nitro)methane (113972-89-7) → 1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-xylopyranosyl cyanide (52443-06-8)

Guidance literature:

With phosphorus trichloride; In pyridine; at 20 ℃;

DOI:10.1016/j.carres.2005.09.012

Reference yield: 35.8%

trimethylsilyl cyanide (7677-24-9) + Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester (68579-19-1) → 1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-xylopyranosyl cyanide (52443-06-8) + 5,5-Dimethyl-2-trimethylsilanyloxy-[1,3,2]dioxaphosphinane 2-sulfide (115010-70-3) + 3,4-di-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-xylopyranose (85326-14-3) + 3,4-di-O-acetyl-1,2-O-<1-(endo-cyano)ethylidene>-α-D-xylopyranose (85326-15-4)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 25h;

DOI:10.1016/S0008-6215(00)00216-0

upstream raw materials:

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-β-D-xylopyranosyl cyanide

2,3,4-tri-O-acetyl-β-D-xylopyranosyl(nitro)methane

trimethylsilyl cyanide

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

2,3,4-tri-O-acetyl-1-deoxy-1-bromo-β-D-xylopyranosyl cyanide

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-bromo-2-cyano-tetrahydro-pyran-3-yl ester

β-D-xylopyranosylmethylamine

2-(5'-Hydroxymethylfuran-2'-yl)thiazole-4-carboxamide