Technology Process of (4R,5R,6R,7R,8S,4'S)-8-(tert-butyldimethylsilanyloxy)-4-(4-methoxy-phenoxy)-5,7-dihydroxy-6-methyl-8-(4'-methyl-2-oxo-[1,3]-dioxolan-4-yl)-oct-enoic acid methyl ester
There total 13 articles about (4R,5R,6R,7R,8S,4'S)-8-(tert-butyldimethylsilanyloxy)-4-(4-methoxy-phenoxy)-5,7-dihydroxy-6-methyl-8-(4'-methyl-2-oxo-[1,3]-dioxolan-4-yl)-oct-enoic acid methyl ester 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:
-
Multi-step reaction with 11 steps
1.1: MgBr2*Et2O / CH2Cl2 / 0.5 h / -25 °C
1.2: 93 percent / CH2Cl2 / -25 - 23 °C
2.1: 92 percent / 2,6-lutidine / CH2Cl2 / 0.83 h / -78 - -50 °C
3.1: (DHQD)2-phal; methanesulfonamide; K2CO3 / K3Fe(CN)6; K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 21 h / 0 °C
4.1: 99 percent / pyridine / CH2Cl2 / 1.5 h / -78 - 0 °C
5.1: 90 percent / DDQ / CH2Cl2 / 1 h / pH 7 / pH 7 buffer
6.1: (COCl)2; DMSO / CH2Cl2 / 0.17 h / -78 °C
7.1: 4.92 g / BF3*Et2O / CH2Cl2 / -78 - -10 °C
8.1: 84 percent / NMO; OsO4 / tetrahydrofuran; acetone; toluene / 48 h / 20 °C / pH7 buffer
9.1: NaIO4 / tetrahydrofuran / 2 h / 20 °C / pH7 buffer
10.1: 88 percent / DBU; LiCl / acetonitrile / 0.83 h / -40 - -5 °C
11.1: 94 percent / PPTS / methanol / 71 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; magnesium bromide;
potassium osmate(VI); potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol;
6.1: Swern oxidation / 10.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo001236o
- Guidance literature:
-
Multi-step reaction with 9 steps
1: (DHQD)2-phal; methanesulfonamide; K2CO3 / K3Fe(CN)6; K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 21 h / 0 °C
2: 99 percent / pyridine / CH2Cl2 / 1.5 h / -78 - 0 °C
3: 90 percent / DDQ / CH2Cl2 / 1 h / pH 7 / pH 7 buffer
4: (COCl)2; DMSO / CH2Cl2 / 0.17 h / -78 °C
5: 4.92 g / BF3*Et2O / CH2Cl2 / -78 - -10 °C
6: 84 percent / NMO; OsO4 / tetrahydrofuran; acetone; toluene / 48 h / 20 °C / pH7 buffer
7: NaIO4 / tetrahydrofuran / 2 h / 20 °C / pH7 buffer
8: 88 percent / DBU; LiCl / acetonitrile / 0.83 h / -40 - -5 °C
9: 94 percent / PPTS / methanol / 71 h / 20 °C
With
pyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride;
potassium osmate(VI); potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol;
4: Swern oxidation / 8: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo001236o
![(4R,5R,6R,7R,8S,4'S)-8-(tert-butyldimethylsilanyloxy)-5-hydroxy-4-(4-methoxy-phenoxy)-6-methyl-8-(4'-methyl-2-oxo-[1,3]-dioxolan-4-yl)-7-triethylsilanyloxy-oct-2-enoic acid methyl ester](/Databaselist/images/loading.webp)
