(2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 358681-52-4
• Molecular Formula: C₅₃H₅₅NO₈S
• Molecular Weight: 866.088
• Mol file: 358681-52-4.mol

Synonyms:(2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property of (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 4 articles about (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 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: 55.0%

benzyl bromide (100-39-0) + (2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester → (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (358681-52-4)

Guidance literature:

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

DOI:10.1039/b102166b

Reference yield:

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (6931-68-6,72690-21-2,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,73208-82-9) → (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (358681-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / BF₃*Et₂O / CH₂Cl₂

2: 100 percent / NaOMe / methanol

3: 55 percent / NaH / dimethylformamide

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b102166b

Reference yield:

para-thiocresol (106-45-6) → (2R,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (358681-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / BF₃*Et₂O / CH₂Cl₂

2: 100 percent / NaOMe / methanol

3: 55 percent / NaH / dimethylformamide

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b102166b

upstream raw materials:

benzyl bromide

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

para-thiocresol

methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-thio-nonulopyranosid)onate

Downstream raw materials:

N-[(2R,3R,4S,6R)-4-Benzyloxy-6-hydroxymethyl-6-p-tolylsulfanyl-2-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-3-yl]-acetamide

Acetic acid (2R,4S,5R,6R)-5-acetylamino-4-benzyloxy-2-p-tolylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-ylmethyl ester