5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose

Base Information

• Chemical Name: 5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose
• CAS No.: 63253-77-0
• Molecular Formula: C₁₆H₁₈O₄S
• Molecular Weight: 306.383
• Mol file: 63253-77-0.mol

Synonyms:

Chemical Property of 5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose

There total 2 articles about 5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose 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:

Didesoxy-5,6-dichloro-6,6-O-isopropylidene-1,2-O-methyl-3-α-D-xylo-hexeno-5-furannose (59578-18-6) → 5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose (63253-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 54.3 percent / N-methylphenylamidure de lithium / diethyl ether / 0.5 h / -60 - 20 °C

2: dimethylformamide / 1.) -50 deg C, 15 min; 2.) 20 deg C, 14 h

With N-methylphenylamidure de lithium; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80850-2

Reference yield:

6-chloro-5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-hex-5-ynofuranose (59578-20-0) + sodium thiophenolate (930-69-8) → 5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-6-phenylthio-α-D-xylo-hex-5-ynofuranose (63253-77-0) + (Z)-6-chloro-5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-5-S-phenyl-5-thio-α-D-xylo-hex-5-enofuranose (78942-94-6)

Guidance literature:

In N,N-dimethyl-formamide; Yield given; 1.) -50 deg C, 15 min; 2.) 20 deg C, 14 h;

DOI:10.1016/S0008-6215(00)80850-2

upstream raw materials:

6-chloro-5,6-didesoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-hex-5-ynofuranose

sodium thiophenolate

Didesoxy-5,6-dichloro-6,6-O-isopropylidene-1,2-O-methyl-3-α-D-xylo-hexeno-5-furannose