2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester
CAS No.:233750-60-2
Molecular Formula:C₄₄H₆₂N₂O₉Si
Molecular Weight:791.07
Hs Code.:

2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

Synonyms:2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

There total 15 articles about 2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl 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:

: 118715-16-5
4-((tert-butyldiphenylsilyl)oxy)butanoic acid

: 233750-60-2
2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

Guidance literature:: Multi-step reaction with 14 steps

2: 1.) DAST, 2.) K₂CO₃ / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) from -78 to 0 deg C

3: 78 percent / BrCCl₃, DBU

4: aq. LiOH / tetrahydrofuran

5: Et₃N

6: CH₂Cl₂ / -20 - 20 °C

7: 82 percent / DAST / CH₂Cl₂ / -78 °C

8: 89 percent / BrCCl₃, DBU / 0.17 h

9: 86 percent / DIBAL / CH₂Cl₂ / -78 °C

10: 1.) Bu₃SnLi, 2.) CuBr*DMS, 3.) (R,R)-4,5-diphenyl-1,3-ditosyl-2-bromo-1,3-diaza-2-borane

11: 93 percent / NaH / dimethylformamide / 0 °C

12: 83 percent / (CF₃CO₂)2IPh / acetonitrile

13: 1.) DABCO, NaHCO₃, K₃Fe(CN)6, OsO₄, 2.) NaIO₄ / 1.) aq. t-BuOH, 2.) aq. THF

14: LiAlH₄, (+)-N-methylephedrine, EtNHC₆H₅ / diethyl ether / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; tri-n-butyltin lithium; Bromotrichloromethane; (R,R)-4,5-diphenyl-1,3-ditosyl-2-bromo-1,3-diaza-2-borane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; (+)-N-methylephedrine; N-ethyl-N-phenylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; bis-[(trifluoroacetoxy)iodo]benzene; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja9904686

Reference yield:

: 233750-53-3
(2S)-2-((2-methyl-1,3-dithian-2-yl)methyl)oxirane

: 233750-60-2
2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / CuI / tetrahydrofuran / -50 °C

2: 82 percent / DMAP, pyridine

3: 1.) Bu₃SnLi, 2.) CuBr*DMS, 3.) (R,R)-4,5-diphenyl-1,3-ditosyl-2-bromo-1,3-diaza-2-borane

4: 93 percent / NaH / dimethylformamide / 0 °C

5: 83 percent / (CF₃CO₂)2IPh / acetonitrile

6: 1.) DABCO, NaHCO₃, K₃Fe(CN)6, OsO₄, 2.) NaIO₄ / 1.) aq. t-BuOH, 2.) aq. THF

7: LiAlH₄, (+)-N-methylephedrine, EtNHC₆H₅ / diethyl ether / -78 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; tri-n-butyltin lithium; (R,R)-4,5-diphenyl-1,3-ditosyl-2-bromo-1,3-diaza-2-borane; sodium hydride; sodium hydrogencarbonate; (+)-N-methylephedrine; N-ethyl-N-phenylamine; bis-[(trifluoroacetoxy)iodo]benzene; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja9904686

Reference yield:

: 233750-65-7
(R)-1-(2-Methyl-[1,3]dithian-2-yl)-4-trimethylsilanylmethyl-pent-4-en-2-ol

: 233750-60-2
2,2-Dimethyl-propionic acid (1R,3R,5R)-5-{2'-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-[2,4']bioxazolyl-4-yl}-3-hydroxy-5-methoxy-1-(2,5,5-trimethyl-[1,3]dioxan-2-ylmethyl)-pentyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / DMAP, pyridine

2: 1.) Bu₃SnLi, 2.) CuBr*DMS, 3.) (R,R)-4,5-diphenyl-1,3-ditosyl-2-bromo-1,3-diaza-2-borane

3: 93 percent / NaH / dimethylformamide / 0 °C

4: 83 percent / (CF₃CO₂)2IPh / acetonitrile

5: 1.) DABCO, NaHCO₃, K₃Fe(CN)6, OsO₄, 2.) NaIO₄ / 1.) aq. t-BuOH, 2.) aq. THF

6: LiAlH₄, (+)-N-methylephedrine, EtNHC₆H₅ / diethyl ether / -78 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; tri-n-butyltin lithium; (R,R)-4,5-diphenyl-1,3-ditosyl-2-bromo-1,3-diaza-2-borane; sodium hydride; sodium hydrogencarbonate; (+)-N-methylephedrine; N-ethyl-N-phenylamine; bis-[(trifluoroacetoxy)iodo]benzene; potassium hexacyanoferrate(III); In diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja9904686