(2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate

Base Information

• Chemical Name: (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate
• CAS No.: 1316108-89-0
• Molecular Formula: C₄₆H₅₀O₈
• Molecular Weight: 730.898
• Mol file: 1316108-89-0.mol

Synonyms:(2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate

Chemical Property of (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate

There total 3 articles about (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate 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: 93.0%

(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate (1316108-84-5) + benzoic acid (65-85-0,8013-63-6) → (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate (1316108-89-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.05.063

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate (1316108-89-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol / 12 h / Inert atmosphere

2: pyridine / dichloromethane / 20 °C / Inert atmosphere

3: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; triphenylphosphine; diethylazodicarboxylate; In ethanol; dichloromethane; toluene; 3: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2011.05.063

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucitol (78136-16-0,14233-48-8) → (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate (1316108-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 20 °C / Inert atmosphere

2: triphenylphosphine; diethylazodicarboxylate / toluene / 20 °C / Inert atmosphere

With pyridine; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; toluene; 2: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2011.05.063

upstream raw materials:

(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexyl pivalate

benzoic acid

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2,3,4,6-tetra-O-benzyl-D-glucitol

Downstream raw materials:

N-(2-hydroxy-ethyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin

(2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol

N-butyldeoxynojirimycin

N-benzyl-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin