(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

Base Information

Chemical Name:(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal
CAS No.:148903-95-1
Molecular Formula:C₂₈H₃₄O₄Si
Molecular Weight:462.661
Hs Code.:

Synonyms:(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

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Chemical Property of (E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

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Technology Process of (E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

There total 8 articles about (E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal 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: 77.0%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: (Z)-(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecine-2-carbaldehyde

: 148903-95-1
(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

Guidance literature:: In dichloromethane; for 16h; Ambient temperature;
DOI:10.1021/ja00066a056

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 148903-95-1
(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

Guidance literature:: Multi-step reaction with 8 steps

1: HCl / diethyl ether / 0.25 h

2: pyridine / 0.5 h / Ambient temperature

3: 98 percent / BCl₃*Me₂S / diethyl ether / 0.17 h / Ambient temperature

4: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C

5: 96 percent

6: 85 percent / HF, pyridine / tetrahydrofuran

7: DMSO, (COCl)2 / -78 °C

8: 77 percent / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; hydrogenchloride; oxalyl dichloride; boron trichloride - methyl sulfide complex; hydrogen fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00066a056

Reference yield:

: 148903-86-0
tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-5-methoxytetrahydrofuran-2-yl)methoxy)diphenylsilane

: 148903-95-1
(E)-3-[(Z)-(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-2-yl]-propenal

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / BCl₃*Me₂S / diethyl ether / 0.17 h / Ambient temperature

2: 1.) NaN(TMS)2 / 1.) toluene, THF, from 0 deg C to -70 deg C, 2.) toluene, THF, from -70 deg C to 0 deg C

3: 96 percent

4: 85 percent / HF, pyridine / tetrahydrofuran

5: DMSO, (COCl)2 / -78 °C

6: 77 percent / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; oxalyl dichloride; boron trichloride - methyl sulfide complex; hydrogen fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00066a056