2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide

Base Information

• Chemical Name: 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide
• CAS No.: 118377-11-0
• Molecular Formula: C₁₇H₂₂NO₃S*I
• Molecular Weight: 447.337
• Mol file: 118377-11-0.mol

Synonyms:2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide

Chemical Property of 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide

There total 12 articles about 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide 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: 94.0%

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol (103795-11-5) + methyl iodide (74-88-4) → 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide (118377-11-0)

Guidance literature:

In acetonitrile; for 7h; Heating;

DOI:10.1021/jo00264a035

Reference yield:

(2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol (103795-10-4) → 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide (118377-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, 2.) Bu₄NI / 1.) THF, reflux, 20 min, 2.) r. t., 14 h

2: acetonitrile / Heating

With tetra-(n-butyl)ammonium iodide; sodium hydride; In acetonitrile;

DOI:10.1055/s-1992-34170

Reference yield:

benzyl bromide (100-39-0) → 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide (118377-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 50percent NaH, 2.) tetra-n-butylammonium iodide / 1.) reflux, 20 min, 2.) room temp., overnight

2: 94 percent / acetonitrile / 7 h / Heating

With tetra-(n-butyl)ammonium iodide; sodium hydride; In acetonitrile;

DOI:10.1021/jo00264a035

upstream raw materials:

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

methyl iodide

benzyl bromide

(2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol

Downstream raw materials:

2-[(1R,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole

2-[(1S,2S)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole

Acetic acid (1R,2S)-2-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethyl ester

(2S,3R)-2-benzyloxy-3,4-isopropylidenedioxy-1-(2-thiazolyl)-1-butanone