(1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol

Base Information

• Chemical Name: (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol
• CAS No.: 126360-31-4
• Molecular Formula: C₂₀H₃₁NO₃SSi
• Molecular Weight: 393.623
• Mol file: 126360-31-4.mol

Synonyms:(1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol

Chemical Property of (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol

There total 3 articles about (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol 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: 86.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-2-Benzyloxymethoxy-1-thiazol-2-yl-propan-1-ol (104470-50-0,104470-51-1,126453-98-3,126453-99-4) → (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol (126360-31-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81092-9

Reference yield:

(S)-(-) ethyl 2-<(benzyloxy)ymethoxy>propanoate (63296-55-9) → (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol (126360-31-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) diethyl ether, -78 deg C, 30 min, 2.) diethyl ether, -78 deg C, 10 min

2: 1.) LiB(Bu-s)3H, 2.) 10percent KOH, 30percent H₂O₂ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C - room temperature, 4 h at room temperature

3: 86 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; n-butyllithium; dihydrogen peroxide; L-Selectride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)81092-9

Reference yield:

2-<(S)-2-(benzyloxymethoxy)propanoyl>thiazole (126360-30-3) → (1R)-1-O-tert-butyldimethylsilyl-2-O-benzyloxymethyl-3-deoxy-1-(2-thiazolyl)-L-glycitol (126360-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LiB(Bu-s)3H, 2.) 10percent KOH, 30percent H₂O₂ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C - room temperature, 4 h at room temperature

2: 86 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; dihydrogen peroxide; L-Selectride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)81092-9

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-2-Benzyloxymethoxy-1-thiazol-2-yl-propan-1-ol

(S)-(-) ethyl 2-<(benzyloxy)ymethoxy>propanoate

2-<(S)-2-(benzyloxymethoxy)propanoyl>thiazole

Downstream raw materials:

(3S,4S)-4-O-benzyloxymethyl-3-O-tert-butyldimethylsilyl-1-(2-thiazolyl)-pent-1-ene

2,3,6-trideoxy-4-O-tert-butyldimethylsilyl-5-O-benzyloxymethyl-L-threo-hexose

2-O-tert-butyldimethylsilyl-3-O-benzyloxymethyl-4-deoxy-L-threose