Technology Process of (2R,4S,5R,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-5-methyl-tetrahydro-pyran-2,4-diol
There total 12 articles about (2R,4S,5R,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-5-methyl-tetrahydro-pyran-2,4-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
mercury(II) perchlorate; water; calcium carbonate;
In
acetonitrile;
at 0 ℃;
for 0.416667h;
DOI:10.1021/ol034037a
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C
1.2: tetrabutylammonium iodide / 36 h / 20 °C
2.1: 10-camphorsulfonic acid / methanol; H2O / 20 °C
3.1: 86 percent / Et3N; DMAP / CH2Cl2 / 20 °C
4.1: 93 percent / TfOH / diethyl ether
5.1: (DHQD)2PYR; K3Fe(CN)6; aq. K2CO3 / K2OsO2(OH)4 / 2-methyl-propan-2-ol / 0 °C
6.1: NaOMe
7.1: 95 percent / SO3*Pyr; DMSO / CH2Cl2 / 0 °C
8.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.67 h / -78 - -50 °C
8.2: CeCl3 / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2.5 h / -78 °C
8.3: 51 percent / ZnCl2 / tetrahydrofuran; diethyl ether; hexamethylphosphoric acid triamide / 4 h / -78 °C
9.1: 86 percent / 10-camphorsulfonic acid; H2O / methanol / 2.5 h / 20 °C
10.1: 95 percent / Hg(ClO4)2*4H2O; CaCO3; H2O / acetonitrile / 0.42 h / 0 °C
With
dmap; n-butyllithium; mercury(II) perchlorate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridine-SO3 complex; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; water; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; calcium carbonate; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
5.1: Sharpless asymmetric dihydroxylation / 7.1: Parikh-Doering oxidation;
DOI:10.1021/ol034037a
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C
1.2: tetrabutylammonium iodide / 36 h / 20 °C
2.1: 10-camphorsulfonic acid / methanol; H2O / 20 °C
3.1: 86 percent / Et3N; DMAP / CH2Cl2 / 20 °C
4.1: 93 percent / TfOH / diethyl ether
5.1: (DHQD)2PYR; K3Fe(CN)6; aq. K2CO3 / K2OsO2(OH)4 / 2-methyl-propan-2-ol / 0 °C
6.1: NaOMe
7.1: 95 percent / SO3*Pyr; DMSO / CH2Cl2 / 0 °C
8.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.67 h / -78 - -50 °C
8.2: CeCl3 / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2.5 h / -78 °C
8.3: 51 percent / ZnCl2 / tetrahydrofuran; diethyl ether; hexamethylphosphoric acid triamide / 4 h / -78 °C
9.1: 86 percent / 10-camphorsulfonic acid; H2O / methanol / 2.5 h / 20 °C
10.1: 95 percent / Hg(ClO4)2*4H2O; CaCO3; H2O / acetonitrile / 0.42 h / 0 °C
With
dmap; n-butyllithium; mercury(II) perchlorate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridine-SO3 complex; trifluorormethanesulfonic acid; (1S)-10-camphorsulfonic acid; water; sodium methylate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; calcium carbonate; potassium hexacyanoferrate(III);
potassium dioxotetrahydroxoosmate(VI);
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
5.1: Sharpless asymmetric dihydroxylation / 7.1: Parikh-Doering oxidation;
DOI:10.1021/ol034037a
![(2S,3S,4R)-8-Benzyloxy-1-(2-{(S)-[(2R,3S,4R,5S)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-[1,3]dithian-2-yl)-3-methyl-octane-2,4-diol](/Databaselist/images/loading.webp)
