phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside
• CAS No.: 864815-48-5
• Molecular Formula: C₃₉H₄₈O₅SSi
• Molecular Weight: 656.959

Synonyms:phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside

Chemical Property of phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside

There total 3 articles about phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-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: 94.0%

phenyl 6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside (864815-47-4) + benzyl bromide (100-39-0) → phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside (864815-48-5)

Guidance literature:

phenyl 6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; for 16h;

DOI:10.1039/b416106h

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside (864815-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / Et₃N; pyridine

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 94 percent / dimethylformamide / 16 h

With pyridine; sodium hydride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/b416106h

Reference yield:

phenyl‐1‐thio‐α‐L‐mannopyranoside (200941-62-4) → phenyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside (864815-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / Et₃N; pyridine

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 94 percent / dimethylformamide / 16 h

With pyridine; sodium hydride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/b416106h

upstream raw materials:

phenyl 6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside

benzyl bromide

tert-butyldimethylsilyl chloride

phenyl‐1‐thio‐α‐L‐mannopyranoside

Downstream raw materials:

methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyluronyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-2-(3-aminopropionamido)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside lactam

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