[5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

Base Information

Chemical Name:[5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester
CAS No.:289505-49-3
Molecular Formula:C₂₅H₄₃NO₆Si
Molecular Weight:481.705
Hs Code.:

[5-benzyloxy-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid <i>tert</i>-butyl ester

Synonyms:[5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

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Chemical Property of [5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

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Technology Process of [5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

There total 11 articles about [5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-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: 99.0%

: [5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

: 289505-49-3
[5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

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

: 289505-49-3
[5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂

2: 96 percent / NaH / dimethylformamide / 0 °C

3: 99 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 20 °C

With camphor-10-sulfonic acid; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Methylation / 3: Hydrolysis;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: 100-39-0
benzyl bromide

: 289505-49-3
[5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 86 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: NaN₃; NH₄Cl / H₂O; 2-methoxy-ethanol / Heating

3.1: BF₃*Et₂O / 20 °C

4.1: 78 percent / Et₃SiH; TMSOTF; BF₃*OEt₂ / CH₂Cl₂; acetonitrile / 20 °C

5.1: NaOMe / methanol / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂

7.1: PPh₃ / tetrahydrofuran / 20 °C

7.2: H₂O / 45 °C

8.1: Et₃N / CH₂Cl₂

9.1: 96 percent / NaH / dimethylformamide / 0 °C

10.1: 99 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 20 °C

With 2,6-dimethylpyridine; triethylsilane; sodium azide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Acetylation / 4.1: Reduction / 5.1: Deacetylation / 6.1: Etherification / 7.1: Reduction / 7.2: Hydrolysis / 8.1: Esterification / 9.1: Methylation / 10.1: Hydrolysis;
DOI:10.1016/S0040-4039(00)00518-9