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

Base Information

• Chemical Name: methyl 3,4-di-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside
• CAS No.: 154796-58-4
• Molecular Formula: C₂₄H₂₇NO₅S
• Molecular Weight: 441.548
• Mol file: 154796-58-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about methyl 3,4-di-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside 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: 90.0%

methanol (67-56-1) + (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) → methyl 3,4-di-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside (154796-58-4)

Guidance literature:

With hydrogenchloride; for 16h; Ambient temperature;

Reference yield:

2-bromo-1-thiazol-2-yl-ethanone (3292-77-1) → methyl 3,4-di-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside (154796-58-4)

Guidance literature:

Multi-step reaction with 5 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

5: 90 percent / HCl / 16 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; chloroform; toluene;

Reference yield:

1-(thiazol-2-yl)-2-(triphenyl-λ 5-phosphanylidene)ethan-1-one (136029-15-7) → methyl 3,4-di-O-benzyl-2-deoxy-1-(2-thiazolyl)-α-D-arabino-hexopyranoside (154796-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / CHCl₃ / 36 h / 25 °C

2: 65 percent / tetrahydrofuran / 5 h / -50 °C

3: 90 percent / HCl / 16 h / Ambient temperature

With hydrogenchloride; In tetrahydrofuran; chloroform;

upstream raw materials:

methanol

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

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