2,3,4,6-Tetrakis-O-(trimethylsilyl)-alpha-D-glucopyranosyl iodide

Base Information

• Chemical Name: 2,3,4,6-Tetrakis-O-(trimethylsilyl)-alpha-D-glucopyranosyl iodide
• CAS No.: 352432-46-3
• Molecular Formula: C₁₈H₄₃IO₅Si₄
• Molecular Weight: 578.783
• Mol file: 352432-46-3.mol

Synonyms:2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranosyl iodide

Chemical Property of 2,3,4,6-Tetrakis-O-(trimethylsilyl)-alpha-D-glucopyranosyl iodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-Tetrakis-O-(trimethylsilyl)-alpha-D-glucopyranosyl iodide

There total 4 articles about 2,3,4,6-Tetrakis-O-(trimethylsilyl)-alpha-D-glucopyranosyl iodide 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:

1,2,3,4,6-penta-O-trimethylsilyl-α-D-glucopyranose (1769-00-2,2775-90-8,3327-61-5,3411-25-4,19126-99-9,24707-99-1,24708-00-7,32166-80-6,32166-97-5,55057-23-3,55057-24-4,55057-25-5,55057-26-6,55521-15-8,55529-69-6,55529-70-9,122798-09-8,122798-11-2,122798-15-6,122798-16-7,122798-18-9,122798-19-0,143729-45-7) → 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranosyl iodide (352432-46-3)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1021/ol0160405

Reference yield:

Pentakis-O-(trimethylsilyl)-D-glucose (1769-00-2,2775-90-8,3327-61-5,3411-25-4,19126-99-9,24707-99-1,24708-00-7,32166-80-6,32166-97-5,55057-23-3,55057-24-4,55057-25-5,55057-26-6,55521-15-8,55529-69-6,55529-70-9,122798-09-8,122798-11-2,122798-15-6,122798-16-7,122798-18-9,122798-19-0,143729-45-7) → 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranosyl iodide (352432-46-3)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201800209

Reference yield:

D-Glucose (2280-44-6) → 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranosyl iodide (352432-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / triethylamine / dimethylformamide / 4 h / 20 °C

2: trimethylsilyl iodide / CH₂Cl₂ / 0.17 h / 20 °C

With trimethylsilyl iodide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0160405

upstream raw materials:

1,2,3,4,6-penta-O-trimethylsilyl-α-D-glucopyranose

D-Glucose

alpha-D-glucopyranose

Pentakis-O-(trimethylsilyl)-D-glucose

Downstream raw materials:

4-hydroxyphenyl α-D-glucopyranoside

Refernces

• 1、 Wang, Hong,Cui, Yanli,Zou, Rong,Cheng, Zhaodong,Yao, Weirong,Mao, Yangyi,Zhang, Yongmin. "Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor". . p. 1 - 5. Retrieved 2016.
• 2、 Boehlich, G. Jacob,Schützenmeister, Nina. "β-Selective C-Glycosylation and its Application in the Synthesis of Scleropentaside A". . p. 5110 - 5113. Retrieved 2019.
• 3、 Cui, Yifan,Huang, Chaofan,Li, Can,Lin, Jie,Liu, Qi,Ma, Shengming,Qin, Anni,Shi, Fuchun,Wang, Huanan,Wu, Guolin,Wu, Penglin,Xiao, Junzhe,Xu, Haibo,Yu, Biao,Yuan, Yuan,Zhai, Yizhan,Zheng, Wei-Feng,Zheng, Yangguangyan. "A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A". . p. 9347 - 9351. Retrieved 2021/07/25.