tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

Base Information

Chemical Name:tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate
CAS No.:1334227-95-0
Molecular Formula:C₂₃H₂₉NO₆
Molecular Weight:415.486
Hs Code.:

Synonyms:tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

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Chemical Property of tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

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Technology Process of tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

There total 14 articles about tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate 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: 95.0%

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

: 1334227-95-0
tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

Guidance literature:: With methanol; potassium carbonate; at 70 ℃; for 0.75h;
DOI:10.1016/j.tetlet.2011.07.035

Reference yield:

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

: 1334227-95-0
tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

Guidance literature:: Multi-step reaction with 10 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

10.1: methanol; potassium carbonate / 0.75 h / 70 °C

With titanium(IV) isopropylate; methanol; sodium azide; p-cumenyl hydroperoxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 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

: 1334227-95-0
tert-butyl (1R,2R)-2-(benzyloxy)-2-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-1-(4-hydroxyphenyl)ethylcarbamate

Guidance literature:: Multi-step reaction with 12 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

12.1: methanol; potassium carbonate / 0.75 h / 70 °C

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium azide; p-cumenyl hydroperoxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 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