(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Base Information

Chemical Name:(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine
CAS No.:174271-53-5
Molecular Formula:C₃₂H₅₅NO₅Si₂
Molecular Weight:589.963
Hs Code.:

Synonyms:(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Suppliers and Price of (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

There total 8 articles about (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 174271-52-4
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-1,5-heptadienyl>oxazolidine

: 174271-53-5
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo9517914

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 174271-53-5
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / SOCl₂ / 24 h / Ambient temperature

2: 95 percent / BF₃*Et₂O / acetone / 25 h

3: 75 percent / DIBAL-H / toluene / 4 h / -78 °C

4: 1.) NaH / 1.) THF, 30 min, 2.) 1 h

5: 79 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C

6: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

8: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; thionyl chloride; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;
DOI:10.1021/jo9517914

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 174271-53-5
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(1E,5E,3S,4S)-3,4-bis<(tert-butyldimethylsilyl)oxy>-1,5-heptadienyl>oxazolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / BF₃*Et₂O / acetone / 25 h

2: 75 percent / DIBAL-H / toluene / 4 h / -78 °C

3: 1.) NaH / 1.) THF, 30 min, 2.) 1 h

4: 79 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C

5: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

7: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;
DOI:10.1021/jo9517914