3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester
• CAS No.: 746656-98-4
• Molecular Formula: C₂₉H₃₉NO₇
• Molecular Weight: 513.631
• Mol file: 746656-98-4.mol

Synonyms:3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester

Chemical Property of 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester

There total 3 articles about 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester 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: 70.0%

tert-butyl alcohol (75-65-0) + N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol (746656-97-3) → 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester (746656-98-4)

Guidance literature:

With chromium trioxide-pyridine complex; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2004.05.118

Reference yield:

6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol (155696-77-8) → 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester (746656-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TsCl; pyridine; DMAP / 3 h / 0 - 20 °C

1.2: K₂CO₃ / methanol / 10 h / 20 °C

2.1: Ph₃P / methanol / 2 h

2.2: methanol

3.1: CrO₃; pyridine; acetic anhydride / CH₂Cl₂; dimethylformamide / 12 h / 20 °C

With pyridine; chromium(VI) oxide; dmap; acetic anhydride; p-toluenesulfonyl chloride; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2007.07.158

Reference yield:

2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol (171973-88-9) → 3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester (746656-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Ph₃P / methanol / 2 h

1.2: methanol

2.1: CrO₃; pyridine; acetic anhydride / CH₂Cl₂; dimethylformamide / 12 h / 20 °C

With pyridine; chromium(VI) oxide; acetic anhydride; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2007.07.158

upstream raw materials:

tert-butyl alcohol

N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol

6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol

2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol