(3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone

Base Information

• Chemical Name: (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone
• CAS No.: 154796-56-2
• Molecular Formula: C₂₆H₂₉NO₅S
• Molecular Weight: 467.586
• Mol file: 154796-56-2.mol

Synonyms:(3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone

Chemical Property of (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone

There total 4 articles about (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone 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: 15.0%

sodium phenyl-methanolate (20194-18-7) + (4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one (154796-50-6) → (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone (154796-56-2) + (3S,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone

Guidance literature:

In tetrahydrofuran; at -50 ℃; for 5h;

Reference yield:

2-bromo-1-thiazol-2-yl-ethanone (3292-77-1) → (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone (154796-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / toluene / 3 h / Ambient temperature

2: 95 percent / 1N aq. NaOH / 0.5 h

3: 83 percent / CHCl₃ / 36 h / 25 °C

4: 65 percent / tetrahydrofuran / 5 h / -50 °C

With sodium hydroxide; In tetrahydrofuran; chloroform; toluene;

Reference yield:

((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide (136029-16-8) → (3R,4S,5R)-3,6-di-O-benzyl-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-1-hexanone (154796-56-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / 1N aq. NaOH / 0.5 h

2: 83 percent / CHCl₃ / 36 h / 25 °C

3: 65 percent / tetrahydrofuran / 5 h / -50 °C

With sodium hydroxide; In tetrahydrofuran; chloroform;

upstream raw materials:

sodium phenyl-methanolate

(4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one

2-bromo-1-thiazol-2-yl-ethanone

1-(thiazol-2-yl)-2-(triphenyl-λ ⁵-phosphanylidene)ethan-1-one

Downstream raw materials:

methyl 3,4,6-tri-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside

methyl 3,4-di-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside