Technology Process of 10-[2-(4,6-dihydroxy-5-hydroxymethyl-3,7,9-trimethyl-dodeca-7,10-dienyl)-[1,3]dithian-2-yl]-3-methoxy-5-(4-methoxy-benzyloxy)-4,6,8-trimethyl-7-triisopropylsilanyloxy-2-(2-trimethylsilanyl-ethoxymethoxy)-undec-8-enoic acid
There total 28 articles about 10-[2-(4,6-dihydroxy-5-hydroxymethyl-3,7,9-trimethyl-dodeca-7,10-dienyl)-[1,3]dithian-2-yl]-3-methoxy-5-(4-methoxy-benzyloxy)-4,6,8-trimethyl-7-triisopropylsilanyloxy-2-(2-trimethylsilanyl-ethoxymethoxy)-undec-8-enoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
lithium hydroxide;
In
tetrahydrofuran;
Heating;
DOI:10.1021/ja0289649
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: TBAI; DIEA / CH2Cl2
2.1: K2CO3 / methanol
3.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.07 h / -78 °C
3.2: 75 percent / tetrahydrofuran / 0.17 h
4.1: SO3*pyr; DMSO
5.1: 80 percent / SmI2 / tetrahydrofuran / -10 °C
6.1: PPTs / methanol
7.1: aq. LiOH / tetrahydrofuran / Heating
With
lithium hydroxide; samarium diiodide; pyridine-SO3 complex; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
4.1: Parikh-Doering oxidation / 5.1: Evans-Tischenko reduction;
DOI:10.1021/ja0289649
- Guidance literature:
-
Multi-step reaction with 22 steps
1.1: DMSO; (COCl)2; NEt3 / -78 - 20 °C
2.1: Bu2BOTf; Et3N
3.1: 2,6-lutidine
4.1: LiBH4 / methanol; diethyl ether
5.1: DMAP; Et3N
6.1: OsO4; NMO
7.1: aq. NaIO4
8.1: 97 percent / toluene / 17 h / -78 °C
9.1: K2CO3 / methanol
10.1: PPTs / acetone
11.1: 9-BBN / tetrahydrofuran; diethyl ether
11.2: aq. H2O2; NaOH / tetrahydrofuran; diethyl ether
12.1: Et3N
13.1: DDQ / H2O
14.1: Dess-Martin periodinane
15.1: K2CO3 / methanol
16.1: 92 percent / (PhO)3PCH3I; DIEA / tetrahydrofuran / 0.42 h
17.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.07 h / -78 °C
17.2: 75 percent / tetrahydrofuran / 0.17 h
18.1: SO3*pyr; DMSO
19.1: 80 percent / SmI2 / tetrahydrofuran / -10 °C
20.1: PPTs / methanol
21.1: aq. LiOH / tetrahydrofuran / Heating
With
2,6-dimethylpyridine; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; samarium diiodide; oxalyl dichloride; pyridine-SO3 complex; di-n-butylboryl trifluoromethanesulfonate; methyltriphenoxyphosphonium iodide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; acetone; toluene;
1.1: Swern oxidation / 8.1: Roush crotylation / 14.1: Dess-Martin oxidation / 15.1: Wittig olefination / 19.1: Parikh-Doering oxidation / 20.1: Evans-Tischenko reduction;
DOI:10.1021/ja0289649
