{(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester
• CAS No.: 101668-62-6
• Molecular Formula: C₂₅H₄₄N₂O₄Si₂
• Molecular Weight: 492.806
• Mol file: 101668-62-6.mol

Synonyms:

Chemical Property of {(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester

There total 17 articles about {(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester 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:

(4S)-4-(methoxycarbonylmethyl)-azetidine-2-one (77881-95-9) → {(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester (101668-62-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / lithium borohydride / 1,2-dimethoxy-ethane / 2 h / 45 - 50 °C

2: 79 percent / boron trifluoride etherate / CH₂Cl₂ / 0.33 h / -20 °C

3: 1.) 1.6 M n-butyllithium, diisopropylamine, 2.) trimethylchlorosilane, 3.) isoamyl nitrite / 1.) hexane/THF, -78 deg C, 2.) hexane/THF, 30 min, -50 deg C, 3.) hexane/THF, -78 deg C, 3 h

4: 75 percent / hydrogen / platinum oxide / ethyl acetate / 8 h / Ambient temperature

5: 91 percent / dioxane / Ambient temperature

6: 94 percent / 1 N HCl / methanol / 2 h / 40 °C

7: triethylamine / dimethylformamide / Ambient temperature

With hydrogenchloride; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; boron trifluoride diethyl etherate; hydrogen; triethylamine; diisopropylamine; isopentyl nitrite; platinum(IV) oxide; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.36.469

Reference yield:

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid (77856-52-1) → {(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester (101668-62-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 43 percent / conc. H₂SO₄ / CH₂Cl₂ / 72 h / Ambient temperature

2: hydrogen / 5 percent Pd/C / H₂O; 2-methyl-propan-2-ol / 6 h / Ambient temperature

3: 55 percent / triphenylphosphine, 2,2'-dipyridyl disulfide / acetonitrile / 2 h / 80 °C

4: 78 percent / lithium borohydride / 1,2-dimethoxy-ethane / 2 h / 45 - 50 °C

5: 55 percent / boron trifluoride etherate / CH₂Cl₂ / 0.33 h / -20 °C

6: 1.) 1.6 M n-butyllithium, diisopropylamine, 2.) p-toluenesulfonyl azide, 3.) trimethylchlorosilane / 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 10 min, 3.) THF/hexane, 1 h, room temperature

7: dioxane / Ambient temperature

8: 1 N HCl / methanol / 2 h / 40 °C

9: triethylamine / dimethylformamide / Ambient temperature

With hydrogenchloride; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; 4-toluenesulfonyl azide; 2,2'-dipyridyldisulphide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; triethylamine; diisopropylamine; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.36.469

Reference yield:

(3R)-3-benzyloxycarbonylamino-4-tert-butyoxycarbonylbutyric acid (83436-45-7) → {(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-carbamic acid benzyl ester (101668-62-6)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogen / 5 percent Pd/C / H₂O; 2-methyl-propan-2-ol / 6 h / Ambient temperature

2: 55 percent / triphenylphosphine, 2,2'-dipyridyl disulfide / acetonitrile / 2 h / 80 °C

3: 78 percent / lithium borohydride / 1,2-dimethoxy-ethane / 2 h / 45 - 50 °C

4: 55 percent / boron trifluoride etherate / CH₂Cl₂ / 0.33 h / -20 °C

5: 1.) 1.6 M n-butyllithium, diisopropylamine, 2.) p-toluenesulfonyl azide, 3.) trimethylchlorosilane / 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 10 min, 3.) THF/hexane, 1 h, room temperature

6: dioxane / Ambient temperature

7: 1 N HCl / methanol / 2 h / 40 °C

8: triethylamine / dimethylformamide / Ambient temperature

With hydrogenchloride; lithium borohydride; n-butyllithium; chloro-trimethyl-silane; 4-toluenesulfonyl azide; 2,2'-dipyridyldisulphide; boron trifluoride diethyl etherate; hydrogen; triethylamine; diisopropylamine; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.36.469

upstream raw materials:

tert-butyldimethylsilyl chloride

(3S,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)-2-azetidinone

(4S)-4-(methoxycarbonylmethyl)-azetidine-2-one

(6R)-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one

Downstream raw materials:

[(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-(2-methoxy-ethyl)-4-oxo-azetidin-3-yl]-carbamic acid benzyl ester

[(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-2-(2-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-carbamic acid benzyl ester

(3S,4R)-3-benzyloxycarbonylamino-4-(2-methoxyethyl)-1-tert-butyldimethylsilyl-2-azetidinone

sodium (3S,4R)-3-<2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-(4-nitrobenzyloxycarbonylmethoxyimino)acetamido>-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate