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

Base Information

• Chemical Name: 5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose
• CAS No.: 84036-72-6
• Molecular Formula: C₁₇H₂₃NO₇
• Molecular Weight: 353.372
• Mol file: 84036-72-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose 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: 97.0%

5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranurono-6,3-lacton (54612-59-8) → 5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose (84036-72-6)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1002/hlca.19820650403

Reference yield: 19.7%

(3aR,5R,6S,6aR)-5-((R)-1-Amino-2-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (14685-99-5,16958-27-3) + benzyl chloroformate (501-53-1,94274-21-2) → 5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-β-L-ido-1,4-furanose (129279-37-4) + 5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose (84036-72-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; 1.) 0 deg C, 2.) room temperature;

DOI:10.1248/cpb.38.293

Reference yield:

(3S,3aR,5R,6S,6aR)-und (3S,3aR,5S,6S,6aR)-5,6-Dihydroxy-2-(2,3:5,6-di-O-isopropyliden-α-D-mannofuranosyl)-perhydrofuro<2,3-d>isoxazol-3-carbonsaeure-(t-butyl)ester → 5-benzyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-α-D-gluco-1,4-furanose (84036-72-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / FeCl₃, CaSO₄ / 1.) 0 deg C, 0.5 h; 2.) RT, 2 h

2: 69 percent / H₂ / Raney-nickel / ethanol / 6 h / 80 °C / 37503 Torr

3: 1M Na₂CO₃, 1M NaHCO₃ / CHCl₃ / 3.5 h / Ambient temperature

4: 87 percent / BuCl/CF₃COOH / 1 h / Ambient temperature

5: 97 percent / LiBH₄ / tetrahydrofuran / 3 h / Ambient temperature

With calcium sulfate; lithium borohydride; n-Butyl chloride; hydrogen; iron(III) chloride; sodium hydrogencarbonate; sodium carbonate; trifluoroacetic acid; nickel; In tetrahydrofuran; ethanol; chloroform;

DOI:10.1002/hlca.19820650403

upstream raw materials:

(3aR,5R,6S,6aR)-5-((R)-1-Amino-2-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

benzyl chloroformate

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

5-Benzyloxycarbonylamino-5-desoxy-1,2-O-isopropyliden-α-D-glucofuranuronsaeure(t-butyl)ester

Downstream raw materials:

N¹-(2,4-Dimethoxybenzyl)-8-epi-kifunensine

nojirimycin

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

thexyldimethylsilyl 3-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-3-thio-β-D-galactopyranoside