[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Base Information

Chemical Name:[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane
CAS No.:610316-27-3
Molecular Formula:C₃₁H₃₉N₃O₄Si
Molecular Weight:545.754
Hs Code.:

Synonyms:[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

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Chemical Property of [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

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Technology Process of [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

There total 6 articles about [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane 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: 94.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 610316-26-2
[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

: 610316-27-3
[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0040-4039(03)01650-2

Reference yield:

: 110426-22-7
5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

: 610316-27-3
[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / NBS; H₂O / toluene / 0.25 h / 20 °C

2.1: 86 percent / CSA / acetone / 2 h / 20 °C

3.1: 75 percent / NaN₃ / dimethylformamide / 5 h / 85 °C

4.1: TFAA; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

4.2: 73 percent / aq. NaHCO₃; NaBH₄ / CH₂Cl₂ / 0.33 h / 0 °C

5.1: 94 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; triethylamine; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 4.1: Pummerer rearrangement;
DOI:10.1016/S0040-4039(03)01650-2

Reference yield:

: 110426-21-6
(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one

: 610316-27-3
[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / DIBAH; ZnCl₂ / tetrahydrofuran / 0.5 h / -78 °C

2.1: 88 percent / NBS; H₂O / toluene / 0.25 h / 20 °C

3.1: 86 percent / CSA / acetone / 2 h / 20 °C

4.1: 75 percent / NaN₃ / dimethylformamide / 5 h / 85 °C

5.1: TFAA; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5.2: 73 percent / aq. NaHCO₃; NaBH₄ / CH₂Cl₂ / 0.33 h / 0 °C

6.1: 94 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; sodium azide; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 5.1: Pummerer rearrangement;
DOI:10.1016/S0040-4039(03)01650-2