(2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

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Chemical Name:(2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol
CAS No.:351379-36-7
Molecular Formula:C₂₁H₃₇N₃O₆Si
Molecular Weight:455.627
Hs Code.:

Synonyms:(2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

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Chemical Property of (2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

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Technology Process of (2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

There total 14 articles about (2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol 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: 76.0%

: {(2S,3R)-3-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-benzyl]-oxiranyl}-methanol

: 351379-36-7
(2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

Guidance literature:: With diisopropoxytitanium diazide; In benzene; at 80 ℃;
DOI:10.1016/S0040-4039(00)00105-2

Reference yield:

: 54700-36-6
2-hydroxy-4-methoxy-3-methylbenzaldehyde

: 351379-36-7
(2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

Guidance literature:: Multi-step reaction with 14 steps

1: 100 percent / K₂CO₃ / acetonitrile / 5 h / Heating

2: 85 percent / H₂O₂; SeO₂; water / 2-methyl-propan-2-ol / 5 h / 40 °C

3: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / 12 h / 80 °C

4: 96 percent / Me₂NPh / toluene / 12 h / 210 °C

5: 87 percent / K₂CO₃ / acetonitrile / 12 h / Heating

6: TBAF / tetrahydrofuran / 1 h

7: pyridine / CH₂Cl₂ / 3 h

8: HCl; H₂O / tetrahydrofuran; propan-2-ol / 12 h

9: 96 percent / Et₂AlCl / CH₂Cl₂ / 12 h

10: 90 percent / K₂CO₃ / CHCl₃; methanol / 12 h / Heating

11: 99 percent / imidazole; DMAP / CH₂Cl₂ / 1 h

12: 94 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

13: 98 percent / (D-DET); Ti(OiPr)4; t-BuOOH / 24 h / -20 °C

14: 76 percent / Ti(OiPr)2(N₃)2 / benzene / 80 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; selenium(IV) oxide; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; diethylaluminium chloride; diisobutylaluminium hydride; potassium carbonate; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; benzene; 1: Etherification / 2: oxidative cleavage / 3: Etherification / 4: p-Claisen rearrangement / 5: Etherification / 6: deprotection / 7: Acylation / 8: Hydrolysis / 9: hydroxymethylation / 10: Etherification / 11: Etherification / 12: deprotection / 13: Epoxidation / 14: acidolysis;
DOI:10.1016/S0040-4039(00)00105-2

Reference yield:

: (E)-4-(2,4-Dimethoxy-5-methoxymethoxy-3-methyl-phenyl)-but-2-en-1-ol

: 351379-36-7
(2S,3S)-3-Azido-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,6-trimethoxy-5-methyl-phenyl]-butane-1,2-diol

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂ / 3 h

2: HCl; H₂O / tetrahydrofuran; propan-2-ol / 12 h

3: 96 percent / Et₂AlCl / CH₂Cl₂ / 12 h

4: 90 percent / K₂CO₃ / CHCl₃; methanol / 12 h / Heating

5: 99 percent / imidazole; DMAP / CH₂Cl₂ / 1 h

6: 94 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

7: 98 percent / (D-DET); Ti(OiPr)4; t-BuOOH / 24 h / -20 °C

8: 76 percent / Ti(OiPr)2(N₃)2 / benzene / 80 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diisopropoxytitanium diazide; water; diethylaluminium chloride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; chloroform; isopropyl alcohol; benzene; 1: Acylation / 2: Hydrolysis / 3: hydroxymethylation / 4: Etherification / 5: Etherification / 6: deprotection / 7: Epoxidation / 8: acidolysis;
DOI:10.1016/S0040-4039(00)00105-2