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

Base Information

• Chemical Name: (4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one
• CAS No.: 154796-50-6
• Molecular Formula: C₁₉H₂₁NO₄S
• Molecular Weight: 359.446
• Mol file: 154796-50-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one 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: 83.0%

4-O-benzyl-2,3-O-isopropylidene-aldehydo-D-erythrose (81801-08-3) + 1-(thiazol-2-yl)-2-(triphenyl-λ 5-phosphanylidene)ethan-1-one (136029-15-7) → (4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one (154796-50-6)

Guidance literature:

In chloroform; at 25 ℃; for 36h;

Reference yield:

2-bromo-1-thiazol-2-yl-ethanone (3292-77-1) → (4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one (154796-50-6)

Guidance literature:

Multi-step reaction with 3 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

With sodium hydroxide; In chloroform; toluene;

Reference yield:

((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide (136029-16-8) → (4S,5R)-6-O-benzyl-4,5,6-trihydroxy-4,5-O-isopropylidene-1-(2-thiazolyl)-2(E)-hexen-1-one (154796-50-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 83 percent / CHCl₃ / 36 h / 25 °C

With sodium hydroxide; In chloroform;

upstream raw materials:

4-O-benzyl-2,3-O-isopropylidene-aldehydo-D-erythrose

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

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

((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide

Downstream raw materials:

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

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

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