Technology Process of (1'S,3S,4S,5S)-3-benzamido-3-hydroxymethyl-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-hydroxyethyl]oxolan-2-one
There total 12 articles about (1'S,3S,4S,5S)-3-benzamido-3-hydroxymethyl-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-hydroxyethyl]oxolan-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
peracetic acid; sodium acetate; sodium bromide;
In
acetic acid;
at 25 - 60 ℃;
for 2.5h;
DOI:10.1021/ja0118338
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 98 percent / imidazole
2.1: 67 percent / PCC; Cellite / CH2Cl2
3.1: 99 percent / FeCl3 / CH2Cl2 / 0 °C / 0.5 Torr
4.1: NaH / tetrahydrofuran / 25 °C / Irradiation
4.2: (η3-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C
4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C
5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C
6.1: 94 percent / aq. OsO4; NMO / CH2Cl2 / 12 h / 25 °C
7.1: 78 percent / peracetic acid; sodium bromide; sodium acetate / acetic acid / 2.5 h / 25 - 60 °C
With
1H-imidazole; peracetic acid; osmium(VIII) oxide; N-methyl-2-indolinone; sodium acetate; silica gel; iron(III) chloride; sodium hydride; (+)-10-camphorsulfonic acid; pyridinium chlorochromate; sodium bromide;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetic acid;
7.1: modified Fleming oxidation;
DOI:10.1021/ja0118338
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 61 percent / tetrahydrofuran / 3 h / -78 - 0 °C
2.1: 94 percent / LiOH / tetrahydrofuran; H2O / 8 h / 25 °C
3.1: 97 percent / DCC / tetrahydrofuran / 12 h / 25 °C
4.1: NaH / tetrahydrofuran / 25 °C / Irradiation
4.2: (η3-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C
4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C
5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C
6.1: 94 percent / aq. OsO4; NMO / CH2Cl2 / 12 h / 25 °C
7.1: 78 percent / peracetic acid; sodium bromide; sodium acetate / acetic acid / 2.5 h / 25 - 60 °C
With
peracetic acid; lithium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; sodium acetate; sodium hydride; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; sodium bromide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid;
7.1: modified Fleming oxidation;
DOI:10.1021/ja0118338
![(1'S,3S,4S,5S)-3-benzamido-3-(dimethylphenylsilyl)methyl-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-hydroxyethyl]oxolan-2-one](/Databaselist/images/loading.webp)
