5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton

Base Information

• Chemical Name: 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton
• CAS No.: 54612-59-8
• Molecular Formula: C₁₇H₁₉NO₇
• Molecular Weight: 349.34
• Mol file: 54612-59-8.mol

Synonyms:5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton

Chemical Property of 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton

There total 20 articles about 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton 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: 87.0%

5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranuronsaeure(t-butyl)ester (84043-09-4) → 5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton (54612-59-8)

Guidance literature:

With n-Butyl chloride; trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1002/hlca.19820650403

Reference yield:

Trifluoro-methanesulfonic acid (3aR,6S,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester (76542-57-9,103357-81-9) → ((3aR,6R,7aR)-2,2-Dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid benzyl ester (43139-78-2,54612-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / NaN₃ / dimethylformamide / 5 h / -20 °C

2: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3: NaHCO₃ / ethyl acetate; H₂O / 0.17 h / 0 °C

With sodium azide; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84755-3

Reference yield:

Trifluoro-methanesulfonic acid (3aR,6R,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester (76542-57-9,103357-81-9) → ((3aR,6S,7aR)-2,2-Dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid benzyl ester (43139-78-2,54612-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃ / dimethylformamide / 1 h / -20 - -10 °C

2: H₂ / 10percent Pd/C / ethyl acetate

3: aq. NaHCO₃ / ethyl acetate; H₂O

With sodium azide; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84755-3

upstream raw materials:

benzyl chloroformate

Trifluoro-methanesulfonic acid (3aR,6R,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester

isopropylidene glucuronolactone

(3aR,6R,7aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one

Downstream raw materials:

nojirimycin

1,5-dideoxy-1,5-imino-D-glucitol

5-(N-benzyloxycarbonyl)amino-5-deoxy-D-glucuronolactone

5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose