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

Base Information

• Chemical Name: 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
• CAS No.: 898224-45-8
• Molecular Formula: C₄₃H₅₈Cl₂N₂O₂₀
• Molecular Weight: 993.841
• Mol file: 898224-45-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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:

(2R,4S,5R,6R)-5-Amino-4-hydroxy-6-[(S)-hydroxy-((R)-2-phenyl-[1,3]dioxolan-4-yl)-methyl]-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester (898224-34-5) → 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 (898224-45-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 502 mg / NaHCO₃ / acetonitrile; H₂O / 0.83 h / 0 °C

2: 87 percent / BH₃*NMe₃; aluminium chloride; 4 Angstroem molecular sieves / tetrahydrofuran / 17 h / 20 °C

3: 78 percent / pyridine / tetrahydrofuran / 1 h / 20 °C

4: 96 percent / 3 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; trifluorormethanesulfonic acid; trimethylamine-borane; 3 A molecular sieve; 4 A molecular sieve; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/ja0613613

Reference yield:

methyl (phenyl 5-amino-8,9-O-benzylidene-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (898224-35-6) → 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 (898224-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / BH₃*NMe₃; aluminium chloride; 4 Angstroem molecular sieves / tetrahydrofuran / 17 h / 20 °C

2: 78 percent / pyridine / tetrahydrofuran / 1 h / 20 °C

3: 96 percent / 3 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; N-iodo-succinimide; aluminium trichloride; trifluorormethanesulfonic acid; trimethylamine-borane; 3 A molecular sieve; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0613613

Reference yield:

methyl (phenyl 5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (898224-36-7) → 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 (898224-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / pyridine / tetrahydrofuran / 1 h / 20 °C

2: 96 percent / 3 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0613613

upstream raw materials:

(2R,4S,5R,6R)-5-Amino-4-hydroxy-6-[(S)-hydroxy-((R)-2-phenyl-[1,3]dioxolan-4-yl)-methyl]-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl (phenyl 5-amino-8,9-O-benzylidene-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

methyl (phenyl 5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

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