1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol

Base Information

• Chemical Name: 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol
• CAS No.: 136738-64-2
• Molecular Formula: C₂₀H₂₅NO₈
• Molecular Weight: 407.42
• Mol file: 136738-64-2.mol

Synonyms:

Chemical Property of 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol

There total 5 articles about 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol 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:

β-D-glucose (492-61-5) → 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol (136738-64-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 42 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 8 h / 40 °C / 2 Torr

2: 69 percent / DBU, 2-hydroxy pyridine, molecular sieves (3 Angstroem) / tetrahydrofuran / 72 h / Ambient temperature

3: 54 percent / Fe / tetrahydrofuran; H₂O / 92 h

4: 1) dimethyl aminopyridine (DMAP), Et₃N, 2) pyridine / 1a THF, 0 deg C, 1 h, 1b) RT, 17 h, 2) 22 h

With pyridine; 2-hydroxypyridin; 3 A molecular sieve; iron; dimethyl aminopyridine; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86545-5

Reference yield:

(4aR,6S,7R,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol (25152-90-3) → 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol (136738-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / DBU, 2-hydroxy pyridine, molecular sieves (3 Angstroem) / tetrahydrofuran / 72 h / Ambient temperature

2: 54 percent / Fe / tetrahydrofuran; H₂O / 92 h

3: 1) dimethyl aminopyridine (DMAP), Et₃N, 2) pyridine / 1a THF, 0 deg C, 1 h, 1b) RT, 17 h, 2) 22 h

With pyridine; 2-hydroxypyridin; 3 A molecular sieve; iron; dimethyl aminopyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(01)86545-5

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 1-acetamido-2,6-anhydro-3,4-di-O-acetyl-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol (136738-64-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 42 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 8 h / 40 °C / 2 Torr

2: 69 percent / DBU, 2-hydroxy pyridine, molecular sieves (3 Angstroem) / tetrahydrofuran / 72 h / Ambient temperature

3: 54 percent / Fe / tetrahydrofuran; H₂O / 92 h

4: 1) dimethyl aminopyridine (DMAP), Et₃N, 2) pyridine / 1a THF, 0 deg C, 1 h, 1b) RT, 17 h, 2) 22 h

With pyridine; 2-hydroxypyridin; 3 A molecular sieve; iron; dimethyl aminopyridine; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86545-5

upstream raw materials:

acetic anhydride

1-amino-2,6-anhydro-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol

β-D-glucose

(4aR,6S,7R,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol