5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole

Base Information

Chemical Name:5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole
CAS No.:639006-83-0
Molecular Formula:C₁₉H₂₇N₇O₄S
Molecular Weight:449.534
Hs Code.:

Synonyms:

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Chemical Property of 5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole

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Technology Process of 5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole

There total 8 articles about 5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole 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:

: 312538-65-1
(S)-2-p-Methoxybenzyloxy-3-pentanone

: 639006-83-0
5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole

Guidance literature:: Multi-step reaction with 9 steps

1.1: Ti(i-PrO)4; TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -78 °C

1.2: 82 percent / CH₂Cl₂ / 2 h / -78 °C

2.1: 92 percent / (Me₄N)HB(OAc)3 / acetonitrile; acetic acid / -40 - 0 °C

3.1: 92 percent / PPTS / CH₂Cl₂ / 24 h / 20 °C

4.1: 396 mg / DDQ / CH₂Cl₂; aq. phosphate buffer / 2 h / 0 °C / pH 7

5.1: Et₃N / CH₂Cl₂ / 4 h / 0 °C

6.1: 250 mg / NaN₃ / dimethylformamide / 22 h / 70 °C

7.1: 91 percent / TBAF*3H₂O / tetrahydrofuran / 0 - 20 °C

8.1: DEAD; Ph₃P / tetrahydrofuran / 4.25 h / 0 - 20 °C

9.1: 82 mg / H₂O₂; (NH₄)2MoO₄ / ethanol; tetrahydrofuran; H₂O / 24 h / 20 °C

With titanium(IV) isopropylate; ammonium molibdate; sodium azide; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; In tetrahydrofuran; phosphate buffer; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 8.1: Mitsunobu reaction;
DOI:10.1021/ol035874f

Reference yield:

: 639006-82-9
(2R,3R,4S,5S,6R)-6-azido-3,5-isopropylidenedioxy-2,4-dimethyl-1-heptanol

: 639006-83-0
5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole

Guidance literature:: Multi-step reaction with 2 steps

1: DEAD; Ph₃P / tetrahydrofuran / 4.25 h / 0 - 20 °C

2: 82 mg / H₂O₂; (NH₄)2MoO₄ / ethanol; tetrahydrofuran; H₂O / 24 h / 20 °C

With ammonium molibdate; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; water; 1: Mitsunobu reaction;
DOI:10.1021/ol035874f

Reference yield:

: (S)-1-{(4S,5S,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanol

: 639006-83-0
5-{(S)-2-[(4S,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propane-1-sulfonyl}-1-phenyl-1H-tetrazole

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 4 h / 0 °C

2: 250 mg / NaN₃ / dimethylformamide / 22 h / 70 °C

3: 91 percent / TBAF*3H₂O / tetrahydrofuran / 0 - 20 °C

4: DEAD; Ph₃P / tetrahydrofuran / 4.25 h / 0 - 20 °C

5: 82 mg / H₂O₂; (NH₄)2MoO₄ / ethanol; tetrahydrofuran; H₂O / 24 h / 20 °C

With ammonium molibdate; sodium azide; tetrabutyl ammonium fluoride; dihydrogen peroxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4: Mitsunobu reaction;
DOI:10.1021/ol035874f