[(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester

Base Information

• Chemical Name: [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester
• CAS No.: 368835-91-0
• Molecular Formula: C₂₅H₄₂N₂O₇Si
• Molecular Weight: 510.703
• Mol file: 368835-91-0.mol

Synonyms:[(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester

Chemical Property of [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester

There total 3 articles about [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl 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:

[(1S,2R)-1-{[1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester → [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester (368835-91-0)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃;

DOI:10.1021/ol0101178

Reference yield:

O-<(tert-Butyl)dimethylsilyl>-N-(methoxycarbonyl)-L-threonin (104198-85-8) → [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester (368835-91-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: SOCl₂; pyridine / CH₂Cl₂ / 25 °C

2.1: silver oxide

2.2: Et₃N / 25 °C

3.1: NaBH₄ / ethanol / 0 °C

With pyridine; sodium tetrahydroborate; thionyl chloride; silver(l) oxide; In ethanol; dichloromethane;

DOI:10.1021/ol0101178

Reference yield:

[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-chlorocarbonyl-propyl]-carbamic acid methyl ester → [(1S,2R)-1-{[Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-carbamoyl}-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-carbamic acid methyl ester (368835-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver oxide

1.2: Et₃N / 25 °C

2.1: NaBH₄ / ethanol / 0 °C

With sodium tetrahydroborate; silver(l) oxide; In ethanol;

DOI:10.1021/ol0101178

upstream raw materials:

O-<(tert-Butyl)dimethylsilyl>-N-(methoxycarbonyl)-L-threonin

Downstream raw materials:

C₃₇H₅₃Cl₃N₄O₁₉

Acetic acid (2S,3R,4R,5R,6S)-4-acetoxy-2-[(R)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1-((2S,3R)-3-hydroxy-2-methoxycarbonylamino-butyrylamino)-propoxy]-6-methyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yl ester