methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate
• CAS No.: 879904-71-9
• Molecular Formula: C₂₆H₂₈Cl₃NO₉S
• Molecular Weight: 636.935
• Mol file: 879904-71-9.mol

Synonyms:methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Chemical Property of methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate

There total 4 articles about methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-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:

benzaldehyde dimethyl acetal (1125-88-8) + methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate (402948-42-9) → methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate (879904-71-9)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/ja0613613

Reference yield:

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate (118977-25-6) → methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate (879904-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 60 °C

2: NEt₃ / acetonitrile; H₂O / 20 °C

3: CSA / acetonitrile / 20 °C

With camphor-10-sulfonic acid; triethylamine; In methanol; water; acetonitrile;

DOI:10.3987/COM-05-S(T)30

Reference yield:

(2R,4S,5R,6R)-5-Amino-4-hydroxy-2-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (367922-37-0) → methyl (phenyl 8,9-O-benzylidene-3,5-dideoxy-2-thio-5-(2,2,2-trichloroethoxycarbonylamino)-D-glycero-β-D-galacto-2-nonulopyranosid)onate (879904-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile; H₂O / 2 h / 20 °C

2: 40.0 g / 10-camphorsulfonic acid / dimethylformamide / 3 h / 20 °C

With (1S)-10-camphorsulfonic acid; triethylamine; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0613613

upstream raw materials:

benzaldehyde dimethyl acetal

methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

(2R,4S,5R,6R)-5-Amino-4-hydroxy-2-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

C₅₂H₆₇Cl₅N₂O₂₁

methyl [octyl 5-amino-5-N,4-O-carbonyl-3,5-dideoxy-8-O-(methyl 5-amino-9-O-benzyl-5-N,4-O-carbonyl-7,8-di-O-chloroacetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranosid]onate

methyl [octyl 7-O-acetyl-5-amino-5-N,4-O-carbonyl-3,5-dideoxy-9-O-(methyl 5-amino-9-O-benzyl-5-N,4-O-carbonyl-7,8-di-O-chloroacetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranosid]onate

methyl [octyl 5-amino-5-N,4-O-carbonyl-3,5-dideoxy-8-O-(methyl 5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranosid]onate