methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate

Base Information

• Chemical Name: methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate
• CAS No.: 171973-90-3
• Molecular Formula: C₂₆H₃₃NO₇
• Molecular Weight: 471.551
• Mol file: 171973-90-3.mol

Synonyms:methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate

Chemical Property of methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate

There total 13 articles about methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S,4R,5R)-5-Azidomethyl-3,4-bis-benzyloxy-tetrahydro-furan-2-carboxylic acid methyl ester → methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate (171973-90-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/00404-0399(50)14024-

Reference yield:

(S)-2-((1R,2S,3S)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-aziridine-1-carboxylic acid tert-butyl ester (200802-95-5) → methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate (171973-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: PDC / dimethylformamide / 12 h / 20 °C

1.2: 0.6 g / diethyl ether / 0 °C

2.1: K₂CO₃ / 1 h / 0 °C

With dipyridinium dichromate; potassium carbonate; In N,N-dimethyl-formamide; 1.1: Oxidation / 1.2: Esterification / 2.1: Ring cleavage;

DOI:10.1021/jo000408e

Reference yield:

(2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran (19139-89-0) → methyl 6-(tert-butyloxycarbonyl)amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-gluconate (171973-90-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 83 percent / aq. HCl / acetic acid / 8 h / 80 - 85 °C

2.1: 87 percent / NaBH₄ / methanol / 0 - 20 °C

3.1: Ph₃P / toluene / 24 h / Heating

4.1: 3.32 g / Ph₃P / toluene / 6 h / 20 °C

5.1: PDC / dimethylformamide / 12 h / 20 °C

5.2: 1.35 g / diethyl ether / 0 °C

With hydrogenchloride; sodium tetrahydroborate; dipyridinium dichromate; triphenylphosphine; In methanol; acetic acid; N,N-dimethyl-formamide; toluene; 1.1: Hydrolysis / 2.1: Reduction / 3.1: cyclocondensation / 4.1: Condensation / 5.1: Oxidation / 5.2: Esterification;

DOI:10.1021/jo000408e

upstream raw materials:

di-tert-butyl dicarbonate

diazomethane

(2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid

methanol

Downstream raw materials:

Boc-Gaa(Bn₂)-Phe-Leu-OMe

(1R,5R,6R,7S)-6,7-Bis-benzyloxy-8-oxa-3-aza-bicyclo[3.2.1]octan-2-one

(2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid