phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 1394311-28-4
• Molecular Formula: C₃₃H₄₀O₅SSi
• Molecular Weight: 576.829
• Mol file: 1394311-28-4.mol

Synonyms:phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 3 articles about phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 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:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (1394311-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di(n-butyl)tin oxide / toluene / 3 h / Reflux

1.2: 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.2 h / 20 °C / Inert atmosphere

2.2: 168 h / 50 °C

With sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; toluene;

DOI:10.1021/ja307266n DOI:10.1021/ja307266n

Reference yield:

benzyl bromide (100-39-0) → phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (1394311-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di(n-butyl)tin oxide / toluene / 3 h / Reflux

1.2: 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.2 h / 20 °C / Inert atmosphere

2.2: 168 h / 50 °C

With sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; toluene;

DOI:10.1021/ja307266n DOI:10.1021/ja307266n

Reference yield:

C27H36O5SSn → phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (1394311-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cesium fluoride / N,N-dimethyl-formamide / 6 h / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere

2.2: 168 h / Heating

With sodium hydride; cesium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jacs.5b06126

upstream raw materials:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

benzyl bromide

Downstream raw materials:

phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranosyl sulfoxide

phenyl 2-[O-2-(trimethylsilylmethyl)allyl]-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranosyl sulfoxide