4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

Base Information

Chemical Name:4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate
CAS No.:1334227-87-0
Molecular Formula:C₃₀H₃₅NO₈S
Molecular Weight:569.676
Hs Code.:

Synonyms:4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

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Chemical Property of 4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

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Technology Process of 4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

There total 14 articles about 4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate 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:

Reference yield: 90.0%

: 1334227-88-1
4-((1R,2S,E)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-5-hydroxypent-3-enyl)phenyl 4-methylbenzenesulfonate

: 1334227-87-0
4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

Guidance literature:: With titanium(IV) isopropylate; p-cumenyl hydroperoxide; D-(-)-diisopropyl tartrate; In dichloromethane; at -25 ℃; for 12h; optical yield given as %ee; Molecular sieve;
DOI:10.1016/j.tetlet.2011.07.035

Reference yield:

: toluene-4-sulfonic acid 4-[(2R,3S)-3-hydroxymethyloxyranyl]phenyl ester

: 1334227-87-0
4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium azide; ammonium chloride / tetrahydrofuran; water / 12 h / 50 °C

2.1: triphenylphosphine / tetrahydrofuran; water / 3 h / 20 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h / 20 °C

4.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C

5.1: diisobutylaluminium hydride / dichloromethane / 3 h / 0 - 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

7.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

7.2: 6 h / 20 °C

8.1: diisobutylaluminium hydride / dichloromethane / 2 h / 0 - 20 °C

9.1: titanium(IV) isopropylate; p-cumenyl hydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane / 12 h / -25 °C / Molecular sieve

With titanium(IV) isopropylate; sodium azide; p-cumenyl hydroperoxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ammonium chloride; toluene-4-sulfonic acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 7.2: Horner-Wadsworth-Emmons olefination / 9.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2011.07.035

Reference yield:

: C₁₈H₁₈O₅S

: 1334227-87-0
4-((1R,2R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)ethyl)phenyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / 0 - 20 °C

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 3 h / -25 °C / Molecular sieve

3.1: sodium azide; ammonium chloride / tetrahydrofuran; water / 12 h / 50 °C

4.1: triphenylphosphine / tetrahydrofuran; water / 3 h / 20 °C

5.1: sodium hydrogencarbonate / tetrahydrofuran; water / 4 h / 20 °C

6.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C

7.1: diisobutylaluminium hydride / dichloromethane / 3 h / 0 - 20 °C

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

9.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

9.2: 6 h / 20 °C

10.1: diisobutylaluminium hydride / dichloromethane / 2 h / 0 - 20 °C

11.1: titanium(IV) isopropylate; p-cumenyl hydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane / 12 h / -25 °C / Molecular sieve

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; p-cumenyl hydroperoxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ammonium chloride; toluene-4-sulfonic acid; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 2.1: Sharpless epoxidation / 9.2: Horner-Wadsworth-Emmons olefination / 11.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2011.07.035