(1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane

Base Information

• Chemical Name: (1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane
• CAS No.: 1046470-62-5
• Molecular Formula: C₂₇H₃₉NO₂SSi
• Molecular Weight: 469.764
• Mol file: 1046470-62-5.mol

Synonyms:(1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane

Chemical Property of (1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane

There total 1 articles about (1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane 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: 95.0%

(1S,2S)-2-[(tert-butyldiphenylsiloxy)methyl]-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane (1046470-51-2) + vinyl magnesium bromide (1826-67-1) → (1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane (1046470-62-5)

Guidance literature:

In toluene; at 110 ℃; stereoselective reaction;

DOI:10.1021/ol8013304

Reference yield:

(1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane (1046470-62-5) → (3S,4S)-3,4-methano-Nα,Nδ,Nω-tri-Cbz-D-arginine (1338719-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / methanol; ethyl acetate / 1.5 h / 20 °C / Inert atmosphere

2: sodium carbonate / tetrahydrofuran; water; toluene / 12 h / 20 °C / Inert atmosphere

3: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 2 h / 0 - 20 °C / Inert atmosphere

4: sodium periodate; potassium permanganate; water; sodium hydrogencarbonate / acetone / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; potassium permanganate; sodium periodate; di-isopropyl azodicarboxylate; water; sodium hydrogencarbonate; sodium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; ethyl acetate; acetone; toluene; 3: Mitsunobu reaction;

DOI:10.1016/j.bmc.2011.08.049

Reference yield:

(1S,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1S)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane (1046470-62-5) → (1S,2S)-1-[(1S)-1-(benzyloxycarbonylamino)-2-propenyl]-2-hydroxymethylcyclopropane (1338719-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / methanol; ethyl acetate / 1.5 h / 20 °C / Inert atmosphere

2: sodium carbonate / tetrahydrofuran; water; toluene / 12 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium carbonate; In tetrahydrofuran; methanol; water; ethyl acetate; toluene;

DOI:10.1016/j.bmc.2011.08.049

upstream raw materials:

(1S,2S)-2-[(tert-butyldiphenylsiloxy)methyl]-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane

vinyl magnesium bromide

Downstream raw materials:

(1S,2S)-1-[(1S)-1-(benzyloxycarbonylamino)-2-propenyl]-2-hydroxymethylcyclopropane

(3S,4S)-3,4-methano-Nα,Nδ,Nω-tri-Cbz-D-arginine