Technology Process of Acetic acid (R)-3-{(4R,5S)-5-[(E)-(1S,4R)-1-(diethyl-isopropyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pent-2-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-butyl ester
There total 13 articles about Acetic acid (R)-3-{(4R,5S)-5-[(E)-(1S,4R)-1-(diethyl-isopropyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pent-2-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 2,6-lutidine
2.1: LiBH4 / methanol; diethyl ether
3.1: DMAP; Et3N
4.1: OsO4; NMO
5.1: aq. NaIO4
6.1: 97 percent / toluene / 17 h / -78 °C
7.1: K2CO3 / methanol
8.1: PPTs / acetone
9.1: 9-BBN / tetrahydrofuran; diethyl ether
9.2: aq. H2O2; NaOH / tetrahydrofuran; diethyl ether
10.1: Et3N
With
2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; acetone; toluene;
6.1: Roush crotylation;
DOI:10.1021/ja0289649
- Guidance literature:
-
Multi-step reaction with 12 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
With
2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; acetone; toluene;
1.1: Swern oxidation / 8.1: Roush crotylation;
DOI:10.1021/ja0289649
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: Bu2BOTf; Et3N
2.1: 2,6-lutidine
3.1: LiBH4 / methanol; diethyl ether
4.1: DMAP; Et3N
5.1: OsO4; NMO
6.1: aq. NaIO4
7.1: 97 percent / toluene / 17 h / -78 °C
8.1: K2CO3 / methanol
9.1: PPTs / acetone
10.1: 9-BBN / tetrahydrofuran; diethyl ether
10.2: aq. H2O2; NaOH / tetrahydrofuran; diethyl ether
11.1: Et3N
With
2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; acetone; toluene;
7.1: Roush crotylation;
DOI:10.1021/ja0289649