Technology Process of (2S,3R,4R,5R,6S)-6-(tert-butyldimethylsilanyloxy)-2-(4-methoxy-phenoxy)-4-methyl-6-((2S)-4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-5-triethylsilanyloxy-3-hydroxyhexanal
There total 13 articles about (2S,3R,4R,5R,6S)-6-(tert-butyldimethylsilanyloxy)-2-(4-methoxy-phenoxy)-4-methyl-6-((2S)-4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-5-triethylsilanyloxy-3-hydroxyhexanal 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 9 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
With
pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide;
potassium osmate(VI); potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
6.1: Swern oxidation;
DOI:10.1021/jo001236o
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 92 percent / 2,6-lutidine / CH2Cl2 / 0.83 h / -78 - -50 °C
2: (DHQD)2-phal; methanesulfonamide; K2CO3 / K3Fe(CN)6; K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 21 h / 0 °C
3: 99 percent / pyridine / CH2Cl2 / 1.5 h / -78 - 0 °C
4: 90 percent / DDQ / CH2Cl2 / 1 h / pH 7 / pH 7 buffer
5: (COCl)2; DMSO / CH2Cl2 / 0.17 h / -78 °C
6: 4.92 g / BF3*Et2O / CH2Cl2 / -78 - -10 °C
7: 84 percent / NMO; OsO4 / tetrahydrofuran; acetone; toluene / 48 h / 20 °C / pH7 buffer
8: NaIO4 / tetrahydrofuran / 2 h / 20 °C / pH7 buffer
With
pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
potassium osmate(VI); potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
5: Swern oxidation;
DOI:10.1021/jo001236o
- Guidance literature:
-
Multi-step reaction with 7 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
With
pyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
potassium osmate(VI); potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
4: Swern oxidation;
DOI:10.1021/jo001236o
