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

Base Information

• Chemical Name: (3S,4S,5S)-6-O-benzyl-4,5-O-isopropyliden-3,4,5,6-tetrahydroxy-1-(2-thiazolyl)-1-hexanone
• CAS No.: 152593-90-3
• Molecular Formula: C₁₉H₂₃NO₅S
• Molecular Weight: 377.461
• Mol file: 152593-90-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3S,4S,5S)-6-O-benzyl-4,5-O-isopropyliden-3,4,5,6-tetrahydroxy-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: 62.0%

2-Acetylthiazole (24295-03-2,260998-74-1) + (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → (R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-thiazol-2-yl-propan-1-one + (3S,4S,5S)-6-O-benzyl-4,5-O-isopropyliden-3,4,5,6-tetrahydroxy-1-(2-thiazolyl)-1-hexanone (152593-90-3)

Guidance literature:

With lithium tert-butoxide; In tetrahydrofuran; hexane; at -50 ℃; for 2h;

DOI:10.1055/s-1993-25967

Reference yield:

(3S,4S,5S)-6-O-benzyl-4,5-O-isopropyliden-3,4,5,6-tetrahydroxy-1-(2-thiazolyl)-1-hexanone (152593-90-3) → (1S,3S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-thiazol-2-yl-propane-1,3-diol + (1S,3R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-thiazol-2-yl-propane-1,3-diol

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -40 ℃; for 24h; Yield given. Yields of byproduct given;

DOI:10.1055/s-1993-25967

Reference yield:

(3S,4S,5S)-6-O-benzyl-4,5-O-isopropyliden-3,4,5,6-tetrahydroxy-1-(2-thiazolyl)-1-hexanone (152593-90-3) → 2-[(4R,6S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-methyl-thiazol-3-ium; iodide

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminum hydride (DIBALH) / tetrahydrofuran; toluene / 1 h / -78 °C

2: camphorsulfonic acid / acetone / 2 h / Ambient temperature

3: acetonitrile / 16 h / Heating

With camphor-10-sulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; acetone; toluene; acetonitrile;

DOI:10.1055/s-1993-25967

upstream raw materials:

2-Acetylthiazole

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde