Technology Process of (2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran
There total 14 articles about (2S,3S,4S,5S)-5-hydroxymethyl-2-(3'-phenylsulfonylsuccinimid-3'-yl)-3,4-dihydroxytetrahydrofuran which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
With
water; trifluoroacetic acid;
at 0 ℃;
for 0.333333h;
DOI:10.1021/jo990195x
- Guidance literature:
-
Multi-step reaction with 11 steps
1: 74 percent / monopotassium phosphate buffer / H2O / 1 h / 20 °C
2: 61 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -78 - 0 °C
3: 84 percent / sodium hydride; 1,3-bis(diphenylphosphino)propane / bis(η3-allyl)di-μ-chlorodipalladium / tetrahydrofuran / 3 h / 0 °C / sonication
4: 89 percent / N-methylmorpholine N-oxide; monopotassium phosphate buffer / osmium tetraoxide / CH2Cl2; H2O / 24 h / 20 °C
5: 92 percent / PPTS / CH2Cl2 / 24 h / 35 °C
6: 97 percent / hydrogen / Pd/C / ethyl acetate / 16 h
7: lead tetraacetate; water / acetone / 1.5 h / 0 - 20 °C
8: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 5 h / 20 °C
9: 40 mg / lithium borohydride / tetrahydrofuran / 1 h / -10 - 20 °C
10: 72 percent / ceric ammonium nitrate / acetonitrile; H2O / 1 h / 0 - 20 °C
11: 84 percent / trifluoroacetic acid; water / 0.33 h / 0 °C
With
lead(IV) acetate; lithium borohydride; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid;
palladium on activated charcoal; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II));
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; acetonitrile;
1: Michael addition / 2: Alkylation / 3: Alkylation / 4: Oxidation / 5: ketalization / 6: Hydrogenolysis / 7: Decarboxylation / 8: Esterification / 9: Reduction / 10: Oxidation / 11: Hydrolysis;
DOI:10.1021/jo990195x
- Guidance literature:
-
Multi-step reaction with 12 steps
2: hydrogen peroxide / acetic acid
3: 61 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / -78 - 0 °C
4: 84 percent / sodium hydride; 1,3-bis(diphenylphosphino)propane / bis(η3-allyl)di-μ-chlorodipalladium / tetrahydrofuran / 3 h / 0 °C / sonication
5: 89 percent / N-methylmorpholine N-oxide; monopotassium phosphate buffer / osmium tetraoxide / CH2Cl2; H2O / 24 h / 20 °C
6: 92 percent / PPTS / CH2Cl2 / 24 h / 35 °C
7: 97 percent / hydrogen / Pd/C / ethyl acetate / 16 h
8: lead tetraacetate; water / acetone / 1.5 h / 0 - 20 °C
9: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 5 h / 20 °C
10: 40 mg / lithium borohydride / tetrahydrofuran / 1 h / -10 - 20 °C
11: 72 percent / ceric ammonium nitrate / acetonitrile; H2O / 1 h / 0 - 20 °C
12: 84 percent / trifluoroacetic acid; water / 0.33 h / 0 °C
With
lead(IV) acetate; lithium borohydride; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; monopotassium phosphate buffer; 1,3-bis-(diphenylphosphino)propane; water; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid;
palladium on activated charcoal; osmium(VIII) oxide; bis(η3-allyl-μ-chloropalladium(II));
In
tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; acetone; acetonitrile;
1: Addition / 2: Oxidation / 3: Alkylation / 4: Alkylation / 5: Oxidation / 6: ketalization / 7: Hydrogenolysis / 8: Decarboxylation / 9: Esterification / 10: Reduction / 11: Oxidation / 12: Hydrolysis;
DOI:10.1021/jo990195x
