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

Base Information

Chemical Name:[(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol
CAS No.:610316-26-2
Molecular Formula:C₁₅H₂₁N₃O₄
Molecular Weight:307.349
Hs Code.:

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

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Chemical Property of [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

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Technology Process of [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

There total 5 articles about [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 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: 73.0%

: 605668-79-9
4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane

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

Guidance literature:: 4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane; With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 0.25h;

With sodium tetrahydroborate; sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 0.333333h;
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

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

Guidance literature:: Multi-step reaction with 4 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

With 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

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

Guidance literature:: Multi-step reaction with 5 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

With 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