(-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

Base Information

Chemical Name:(-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol
CAS No.:131380-44-4
Molecular Formula:C₃₀H₃₆O₃Si
Molecular Weight:472.7
Hs Code.:

Synonyms:(-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

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Chemical Property of (-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

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Technology Process of (-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

There total 7 articles about (-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol 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: 87.0%

: 100-39-0
benzyl bromide

: 131380-36-4
(-)-lyxo-(4S,5S,6S)-7-(tert-butyldiphenylsiloxy)-5,6-epoxyhept-1-en-4-ol

: 131380-44-4
(-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 23 ℃; for 12h;
DOI:10.1021/jo00004a053

Reference yield:

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

: 131380-44-4
(-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / PCC, Celite / CH₂Cl₂ / 2 h / 25 °C

2: 93 percent / DIBAL-H / diethyl ether; hexane / 1) -78 deg C, 25 min, 2) 25 deg C, 1h

3: 1) Ti(OiPr)4, (+)-(R,R)-diethyl tartrate, mol. sieves 4 Angstroem, 2) t-BuOOH / 1) CH₂Cl₂, -20 deg C, 30 min, 2) CH₂Cl₂, -20 deg C, 3d

4: 92 percent / PCC, NaOAc, mol. sieves 4 Angstroem, Celite / CH₂Cl₂ / 0.5 h / 25 °C

5: mol. sieves 4 Angstroem / toluene / -78 °C

6: 87 percent / NaH / tetrahydrofuran / 12 h / 23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Celite; sodium acetate; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo00004a053

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 131380-44-4
(-)-lyxo-(4S,5S,6S)-7-(t-butyldiphenylsiloxy)-5,6-epoxy-4-(benzyloxy)hept-1-en-7-ol

Guidance literature:: Multi-step reaction with 7 steps

1: n-BuLi / tetrahydrofuran; hexane / 1) -78 to 25 deg C, 30 min, 2) 3.5h, reflux

2: 99 percent / PCC, Celite / CH₂Cl₂ / 2 h / 25 °C

3: 93 percent / DIBAL-H / diethyl ether; hexane / 1) -78 deg C, 25 min, 2) 25 deg C, 1h

4: 1) Ti(OiPr)4, (+)-(R,R)-diethyl tartrate, mol. sieves 4 Angstroem, 2) t-BuOOH / 1) CH₂Cl₂, -20 deg C, 30 min, 2) CH₂Cl₂, -20 deg C, 3d

5: 92 percent / PCC, NaOAc, mol. sieves 4 Angstroem, Celite / CH₂Cl₂ / 0.5 h / 25 °C

6: mol. sieves 4 Angstroem / toluene / -78 °C

7: 87 percent / NaH / tetrahydrofuran / 12 h / 23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; 4 A molecular sieve; Celite; sodium acetate; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo00004a053