methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS No.: 178685-40-0
• Molecular Formula: C₂₇H₃₄N₂O₁₄S
• Molecular Weight: 642.638
• Mol file: 178685-40-0.mol

Synonyms:methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Chemical Property of methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

There total 1 articles about methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 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: 67.0%

2-Thiosialic acid methyl ester peracetate (104556-69-6) + 1-bromomethyl-4-nitro-benzene (100-11-8) → methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (178685-40-0)

Guidance literature:

2-Thiosialic acid methyl ester peracetate; With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

1-bromomethyl-4-nitro-benzene; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(00)00201-7

Reference yield: 55.0%

methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (178685-40-0) → methyl (S-4-aminobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (325469-98-5)

Guidance literature:

With tin(ll) chloride; In ethanol; at 70 ℃; for 15h;

DOI:10.1016/S0968-0896(00)00201-7

Reference yield:

methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (178685-40-0) → S-D-biotinoyl-4-aminobenzyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonic acid

Guidance literature:

Multi-step reaction with 3 steps

1.1: 55 percent / SnCl₂*2H₂O / ethanol / 15 h / 70 °C

2.1: 71 percent / O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium BF₄^- / dimethylformamide / 0.33 h / 20 °C

3.1: NaOMe / methanol / 0 - 20 °C

3.2: 58 percent / aq. NaOH / H₂O / 16 h / 20 °C / pH 12

With sodium methylate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; tin(ll) chloride; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(00)00201-7

upstream raw materials:

2-Thiosialic acid methyl ester peracetate

1-bromomethyl-4-nitro-benzene

Downstream raw materials:

methyl (S-4-aminobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate

methyl (S-D-biotinoyl-4-aminobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate