Technology Process of (2S)-2-[(1S,2R,3S,4R,5S)-2,3,4,5-tetrakis-benzyloxy-cyclohexyl]-1,4-dioxa-spiro[4.5]decane
There total 12 articles about (2S)-2-[(1S,2R,3S,4R,5S)-2,3,4,5-tetrakis-benzyloxy-cyclohexyl]-1,4-dioxa-spiro[4.5]decane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(1S,2R,3R,4S,6S)-3,6-bis-benzyloxy-4-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]-cyclohexane-1,2-diol;
With
sodium hydride;
In
tetrahydrofuran;
at 20 ℃;
for 2h;
benzyl bromide;
With
N,N,N,N,N,N-hexamethylphosphoric triamide;
In
tetrahydrofuran;
at 20 ℃;
for 12h;
DOI:10.1021/jo061717t
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 3 h
2.1: 92 percent / LiAlH4 / diethyl ether / 1 h / -60 °C
3.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C
4.1: 89 percent / m-CPBA / 1,2-dichloro-ethane / 8 h / 20 °C
5.1: diphenyl diselenide; sodium borohydride / ethanol / 2 h / 20 °C
5.2: 41 percent / aq. H2O2 / ethanol; tetrahydrofuran / 1.5 h / 70 °C
6.1: NaH / tetrahydrofuran / 2 h / 20 °C
6.2: 69 percent / HMPA / tetrahydrofuran / 12 h / 20 °C
7.1: 85 percent / N-methylmorpholine N-oxide monohydrate / OsO4 / acetone; H2O / 16 h / 20 °C
8.1: NaH / tetrahydrofuran / 2 h / 20 °C
8.2: 72 percent / HMPA / tetrahydrofuran / 12 h / 20 °C
With
dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; diphenyl diselenide; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
osmium(VIII) oxide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone;
1.1: Swern oxidation;
DOI:10.1021/jo061717t
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: NaH / tetrahydrofuran / 2 h / 20 °C
1.2: 69 percent / HMPA / tetrahydrofuran / 12 h / 20 °C
2.1: 85 percent / N-methylmorpholine N-oxide monohydrate / OsO4 / acetone; H2O / 16 h / 20 °C
3.1: NaH / tetrahydrofuran / 2 h / 20 °C
3.2: 72 percent / HMPA / tetrahydrofuran / 12 h / 20 °C
With
sodium hydride; 4-methylmorpholine N-oxide;
osmium(VIII) oxide;
In
tetrahydrofuran; water; acetone;
DOI:10.1021/jo061717t
![(1S,2R,3R,4S,6S)-3,6-bis-benzyloxy-4-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]-cyclohexane-1,2-diol](/Databaselist/images/loading.webp)
