2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol

Base Information

• Chemical Name: 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol
• CAS No.: 136738-66-4
• Molecular Formula: C₁₅H₂₁NO₇
• Molecular Weight: 327.334
• Mol file: 136738-66-4.mol

Synonyms:2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol

Chemical Property of 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol

There total 9 articles about 2,6-anhydro-1-benzyloxycarboxamido-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: 100.0%

2,6-anhydro-5,7-O-benzylidene-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol (136738-65-3) → 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol (136738-66-4)

Guidance literature:

With acetic acid; at 90 ℃; for 0.5h;

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

Reference yield:

nitromethyl β-D-glucopyranoside (81846-60-8) + sodium hydrogencarbonate (144-55-8) + benzyl chloroformate (501-53-1,94274-21-2) → 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol (136738-66-4)

Guidance literature:

Pd-C; palladium; In methanol; water; acetone;

Reference yield:

β-D-glucose (492-61-5) → 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol (136738-66-4)

Guidance literature:

Multi-step reaction with 5 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: 98 percent / NaHCO₃ / toluene; tetrahydrofuran; H₂O / 18 h

5: 100 percent / aq. acetic acid / 0.5 h / 90 °C

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

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

upstream raw materials:

nitromethyl β-D-glucopyranoside

benzyl chloroformate

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

D-Glucose

Downstream raw materials:

(2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid