methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate
• CAS No.: 139684-71-2
• Molecular Formula: C₄₆H₄₉NO₉S
• Molecular Weight: 791.962
• Mol file: 139684-71-2.mol

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

There total 17 articles about methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate 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: 45.0%

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-D-erythro-L-gluco-2-nonulopyranosonate (129234-78-2,129263-75-8,134258-00-7) + thiophenol (108-98-5) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (139684-71-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; 0 deg C, 2h, then room temp., 1h;

DOI:10.1016/S0040-4020(01)97586-6

Reference yield:

(3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (128596-95-2,129234-79-3,129234-81-7,139684-71-2) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (139684-71-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; Yield given; 0 deg C, 2h, then room temp., 30 min.;

DOI:10.1016/S0040-4020(01)97586-6

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-D-erythro-L-manno-2-nonulopyranosonate (129234-78-2,129263-75-8,134258-00-7) + thiophenol (108-98-5) → (3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (128596-95-2,129234-79-3,129234-81-7,139684-71-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; 0 deg C, 2h, then room temp., 1h;

DOI:10.1016/S0040-4020(01)97586-6

upstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-D-erythro-L-manno-2-nonulopyranosonate

thiophenol

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

Downstream raw materials:

O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose