(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 168072-96-6
• Molecular Formula: C₄₇H₄₉NO₁₀
• Molecular Weight: 787.907
• Mol file: 168072-96-6.mol

Synonyms:

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 5 articles about (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl 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:

2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester (4539-78-0) + 2-Isocyanatomethyl-benzoic acid tert-butyl ester (168072-86-4) → (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (168072-96-6)

Guidance literature:

With triethylamine; In toluene; at 65 ℃;

DOI:10.1016/0040-4039(95)00049-I

Reference yield:

homophthalic anhydride (703-59-3) → (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (168072-96-6)

Guidance literature:

Multi-step reaction with 5 steps

1: DMAP

2: H₂SO₄ / CH₂Cl₂

3: Pd(PPh₃)4, morpholine / tetrahydrofuran

4: (PhO)2P(O)N₃, Et₃N / toluene / 65 °C

5: Et₃N / toluene / 65 °C

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0040-4039(95)00049-I

Reference yield:

2-Carboxymethyl-benzoic acid tert-butyl ester (168072-81-9) → (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-(2-tert-butoxycarbonyl-benzylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (168072-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (PhO)2P(O)N₃, Et₃N / toluene / 65 °C

2: Et₃N / toluene / 65 °C

With diphenyl phosphoryl azide; triethylamine; In toluene;

DOI:10.1016/0040-4039(95)00049-I

upstream raw materials:

2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester

2-Isocyanatomethyl-benzoic acid tert-butyl ester

homophthalic anhydride

2-Carboxymethyl-benzoic acid tert-butyl ester