Technology Process of (2R,4R,10S)-1-benzyloxy-4-methyl-2,10-bis(tetrahydro-2H-pyran-2-yloxy)undecan-6-one
There total 13 articles about (2R,4R,10S)-1-benzyloxy-4-methyl-2,10-bis(tetrahydro-2H-pyran-2-yloxy)undecan-6-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2R,4R,10S)-1-benzyloxy-8-hydroxy-4-methyl-2,10-bis(tetrahydro-2H-pyran-2-yloxy)undecan-6-one;
With
methanesulfonyl chloride; triethylamine;
In
chloroform;
at 0 ℃;
for 2h;
With
sodium tetrahydroborate; nickel(II) chloride hexahydrate;
In
tetrahydrofuran; methanol;
at 0 ℃;
for 1.08333h;
Cooling;
DOI:10.1134/S1070428014030178
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: nickel(II) chloride hexahydrate; boric acid; sodium tetrahydroborate / water; tetrahydrofuran / 0.67 h / 0 °C / Cooling
2.1: triethylamine / 48 h
3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / Reflux
4.1: titanium(IV) isopropylate; cyclohexylmagnesium bromide / tetrahydrofuran / 16 h
5.1: chromium(VI) oxide; sodium acetate trihydrate / water; acetone / 1 h / -15 °C
6.1: triethylamine; methanesulfonyl chloride / chloroform / 2 h / 0 °C
6.2: 1.08 h / 0 °C / Cooling
With
chromium(VI) oxide; titanium(IV) isopropylate; sodium tetrahydroborate; nickel(II) chloride hexahydrate; boric acid; sodium acetate trihydrate; pyridinium p-toluenesulfonate; methanesulfonyl chloride; triethylamine; cyclohexylmagnesium bromide;
In
tetrahydrofuran; dichloromethane; chloroform; water; acetone;
DOI:10.1134/S1070428014030178
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: titanium(IV) isopropylate; trifluoroacetic acid; (R)-1,1'-Bi-2-naphthol / toluene / 168 h / -30 - -15 °C / Molecular sieve
2.1: nickel(II) chloride hexahydrate; boric acid; sodium tetrahydroborate / water; tetrahydrofuran / 0.67 h / 0 °C / Cooling
3.1: triethylamine / 48 h
4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / Reflux
5.1: titanium(IV) isopropylate; cyclohexylmagnesium bromide / tetrahydrofuran / 16 h
6.1: chromium(VI) oxide; sodium acetate trihydrate / water; acetone / 1 h / -15 °C
7.1: triethylamine; methanesulfonyl chloride / chloroform / 2 h / 0 °C
7.2: 1.08 h / 0 °C / Cooling
With
chromium(VI) oxide; titanium(IV) isopropylate; sodium tetrahydroborate; nickel(II) chloride hexahydrate; (R)-1,1'-Bi-2-naphthol; boric acid; sodium acetate trihydrate; pyridinium p-toluenesulfonate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; cyclohexylmagnesium bromide;
In
tetrahydrofuran; dichloromethane; chloroform; water; acetone; toluene;
1.1: |Keck Asymmetric Allylation;
DOI:10.1134/S1070428014030178
