(R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane

Base Information

• Chemical Name: (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane
• CAS No.: 885321-33-5
• Molecular Formula: C₂₇H₄₁NO₇SSi
• Molecular Weight: 551.777
• Mol file: 885321-33-5.mol

Synonyms:(R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane

Chemical Property of (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane

There total 3 articles about (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane 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: 93.0%

(R)-2-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)ethanol (885321-32-4) + methanesulfonyl chloride (124-63-0) → (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane (885321-33-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2005.12.027

Reference yield:

(R)-tert-butyl 2-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)acetate (885321-31-3) → (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane (885321-33-5)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL-H / toluene; CH₂Cl₂ / -78 - 0 °C

2: 6.275 g / LiBH₄ / diethyl ether / 12 h / 20 °C

3: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With lithium borohydride; diisobutylaluminium hydride; triethylamine; In diethyl ether; dichloromethane; toluene;

DOI:10.1016/j.tetasy.2005.12.027

Reference yield:

tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate (198417-69-5) → (R)-1-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)-2-(methanesulfonyloxy)ethane (885321-33-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / aq. NaOH; TBAI / toluene / 3 h / 0 - 5 °C

2: DIBAL-H / toluene; CH₂Cl₂ / -78 - 0 °C

3: 6.275 g / LiBH₄ / diethyl ether / 12 h / 20 °C

4: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; lithium borohydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; In diethyl ether; dichloromethane; toluene;

DOI:10.1016/j.tetasy.2005.12.027

upstream raw materials:

(R)-2-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)ethanol

methanesulfonyl chloride

(R)-tert-butyl 2-(2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsilyloxy)propoxy)acetate

tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate

Downstream raw materials:

(R)-3-(tert-butyldiphenylsilyloxymethyl)morpholine