Technology Process of 13-Oxa-1,5-dithiaspiro[5.17]tricos-21-en-14-one,
10-hydroxy-11-[(1S,2E,4S,5Z)-1-hydroxy-2,4-dimethyl-2,5-heptadienyl]-
16-methoxy-18-[(4-methoxyphenyl)methoxy]-9,17,19,21,23-pentamethyl
-15-[[2-(trimethylsilyl)ethoxy]methoxy]-20-[[tris(1-methylethyl)silyl]oxy]-,
(9R,10R,11S,15R,16S,17R,18R,19S,20R,21E,23S)-
There total 29 articles about 13-Oxa-1,5-dithiaspiro[5.17]tricos-21-en-14-one,
10-hydroxy-11-[(1S,2E,4S,5Z)-1-hydroxy-2,4-dimethyl-2,5-heptadienyl]-
16-methoxy-18-[(4-methoxyphenyl)methoxy]-9,17,19,21,23-pentamethyl
-15-[[2-(trimethylsilyl)ethoxy]methoxy]-20-[[tris(1-methylethyl)silyl]oxy]-,
(9R,10R,11S,15R,16S,17R,18R,19S,20R,21E,23S)- 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:
- Guidance literature:
-
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;
With
N-ethyl-N,N-diisopropylamine; 2,4,6-trichlorobenzoyl chloride;
In
tetrahydrofuran;
With
dmap;
In
toluene;
Further stages.;
DOI:10.1021/ja0289649
- Guidance literature:
-
Multi-step reaction with 8 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
8.1: 2,4,5-trichlorobenzoyl chloride; DIEA / tetrahydrofuran
8.2: DMAP / toluene
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; 2,4,6-trichlorobenzoyl chloride;
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 23 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
22.1: 2,4,5-trichlorobenzoyl chloride; DIEA / tetrahydrofuran
22.2: DMAP / toluene
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; 2,4,6-trichlorobenzoyl chloride;
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
![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](/Databaselist/images/loading.webp)
