Technology Process of (2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-ol
There total 12 articles about (2R,3R,4S,5R,6R)-4-Benzyloxy-6-methoxy-2-methyl-5-phenylsulfanyl-tetrahydro-pyran-3-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 91 percent / LiEt3BH / tetrahydrofuran / 1 h / -40 °C
2.1: 95 percent / Et3N; DMAP / CH2Cl2 / 0.25 h / 0 °C
3.1: 90 percent / Grubbs' catalyst / CH2Cl2 / 34 h / 35 °C
4.1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C
5.1: 90 percent / NMO; OsO4; H2O / acetone / 12 h / 25 °C
6.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1 h / 0 - 25 °C
7.1: 69 percent / BF3*Et2O / CH2Cl2 / 1 h / -20 °C
8.1: 97 percent / K2CO3; MeOH / diethyl ether / 1 h / 25 °C
9.1: nBu2SnO / toluene / 3 h / Heating
9.2: 80 percent / nBu4NI / toluene / 2 h / Heating
10.1: DAST / CH2Cl2 / 0.5 h / 0 °C
11.1: 0.220 g / SnCl2; molecular sieves 4 Angstroem / CH2Cl2 / 12 h / -10 °C
12.1: 94 percent / TBAF / tetrahydrofuran / 1 h / 25 °C
With
methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; di(n-butyl)tin oxide; lithium triethylborohydride; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride;
Grubbs catalyst first generation;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;
1.1: Reduction / 2.1: Esterification / 3.1: Cyclization / 4.1: Reduction / 5.1: Addition / 6.1: Acetylation / 7.1: Substitution / 8.1: Deacetylation / 9.1: Cyclization / 9.2: Ring cleavage / 10.1: Substitution / 11.1: Etherification / 12.1: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 90 percent / Grubbs' catalyst / CH2Cl2 / 34 h / 35 °C
2.1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C
3.1: 90 percent / NMO; OsO4; H2O / acetone / 12 h / 25 °C
4.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1 h / 0 - 25 °C
5.1: 69 percent / BF3*Et2O / CH2Cl2 / 1 h / -20 °C
6.1: 97 percent / K2CO3; MeOH / diethyl ether / 1 h / 25 °C
7.1: nBu2SnO / toluene / 3 h / Heating
7.2: 80 percent / nBu4NI / toluene / 2 h / Heating
8.1: DAST / CH2Cl2 / 0.5 h / 0 °C
9.1: 0.220 g / SnCl2; molecular sieves 4 Angstroem / CH2Cl2 / 12 h / -10 °C
10.1: 94 percent / TBAF / tetrahydrofuran / 1 h / 25 °C
With
methanol; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride;
Grubbs catalyst first generation;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;
1.1: Cyclization / 2.1: Reduction / 3.1: Addition / 4.1: Acetylation / 5.1: Substitution / 6.1: Deacetylation / 7.1: Cyclization / 7.2: Ring cleavage / 8.1: Substitution / 9.1: Etherification / 10.1: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4
