(-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

Base Information

Chemical Name:(-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene
CAS No.:131484-28-1
Molecular Formula:C₃₀H₃₅NO₄Si
Molecular Weight:501.698
Hs Code.:

Synonyms:(-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

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Chemical Property of (-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

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Technology Process of (-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

There total 5 articles about (-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene 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: 73.0%

: 131484-25-8
(+)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxyhept-1-en-4-ol

: 103-71-9
phenyl isocyanate

: 131484-28-1
(-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

Guidance literature:: With pyridine; In dichloromethane; at 25 ℃;
DOI:10.1021/jo00004a053

Reference yield:

: 87770-83-0
(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol

: 131484-28-1
(-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 1) Ti(OiPr)4, (-)-(S,S)-diethyl tartrate, molecular sieves 4 Angstroem, 2) t-BuOOH / 1) CH₂Cl₂, -20 deg C, 30 min, 2) CH₂Cl₂, -20 deg C, 4d

2: PCC, NaOAc, mol. sieves 4 Angstroem, Celite / CH₂Cl₂ / 0.5 h / 25 °C

3: 93 percent / mol. sieves 4 Angstroem / toluene / -78 °C

4: 73 percent / pyridine / CH₂Cl₂ / 25 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; Celite; sodium acetate; (-)-diethyl tartrate; pyridinium chlorochromate; In dichloromethane; toluene;
DOI:10.1021/jo00004a053

Reference yield:

: 131484-41-8
erythro-(2R,3S)-4-(tert-butyldimethylsiloxy)-2,3-epoxy-1-butanol

: 131484-28-1
(-)-ribo-(4R,5R,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxy-4-<(phenylcarbamoyl)oxy>hept-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1: PCC, NaOAc, mol. sieves 4 Angstroem, Celite / CH₂Cl₂ / 0.5 h / 25 °C

2: 93 percent / mol. sieves 4 Angstroem / toluene / -78 °C

3: 73 percent / pyridine / CH₂Cl₂ / 25 °C

With pyridine; 4 A molecular sieve; Celite; sodium acetate; pyridinium chlorochromate; In dichloromethane; toluene;
DOI:10.1021/jo00004a053