{3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:{3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester
CAS No.:364631-76-5
Molecular Formula:C₄₄H₇₂N₄O₉Si₃
Molecular Weight:885.334
Hs Code.:

{3-[3-azido-4,5-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid <i>tert</i>-butyl ester

Synonyms:{3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

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Chemical Property of {3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

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Technology Process of {3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

There total 9 articles about {3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester 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:

: [5-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-ylethynyl]-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yl]-carbamic acid tert-butyl ester

: 364631-76-5
{3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

Guidance literature:: With water; acetic acid; In methanol; at 20 ℃; for 12h;
DOI:10.1016/S0040-4020(01)00545-2

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 364631-76-5
{3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 82 percent / NaHCO₃ / tetrahydrofuran; H₂O / 18 h / 20 °C

2.1: 85 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 2.75 h / -78 °C

3.1: LDA / tetrahydrofuran / 0.75 h / -78 °C

3.2: tetrahydrofuran / 1 h / -78 °C

4.1: Et₃N / CH₂Cl₂ / 18 h / 20 °C

5.1: 24.40 mmol / MeLi / diethyl ether; tetrahydrofuran / -51 - 0 °C

6.1: 100 percent / p-TsOH*H₂O / methanol / 12 h / 20 °C

7.1: 5.3 mmol / camphorsulfonic acid / dimethylformamide / 20 - 40 °C

8.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.5 h / -78 °C

8.2: tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.33 h / -78 °C

9.1: AcOH; H₂O / methanol / 12 h / 20 °C

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; water; methyllithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00545-2

Reference yield:

: 364631-73-2
tert-butyl 5-formyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

: 364631-76-5
{3-[3-azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1,1-bis-hydroxymethyl-prop-2-ynyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / 0.75 h / -78 °C

1.2: tetrahydrofuran / 1 h / -78 °C

2.1: Et₃N / CH₂Cl₂ / 18 h / 20 °C

3.1: 24.40 mmol / MeLi / diethyl ether; tetrahydrofuran / -51 - 0 °C

4.1: 100 percent / p-TsOH*H₂O / methanol / 12 h / 20 °C

5.1: 5.3 mmol / camphorsulfonic acid / dimethylformamide / 20 - 40 °C

6.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.5 h / -78 °C

6.2: tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.33 h / -78 °C

7.1: AcOH; H₂O / methanol / 12 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; water; methyllithium; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00545-2