{(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane
• CAS No.: 639006-74-9
• Molecular Formula: C₂₈H₄₁N₃O₃Si
• Molecular Weight: 495.737

Synonyms:{(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane

Chemical Property of {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane

There total 7 articles about {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-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:

Methanesulfonic acid (S)-1-{(4S,5S,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl ester → {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane (639006-74-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 22h;

DOI:10.1021/ol035874f

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane (639006-74-9)

Guidance literature:

Multi-step reaction with 6 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

With titanium(IV) isopropylate; sodium azide; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In phosphate buffer; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol035874f

Reference yield:

(S)-2-p-Methoxybenzyloxy-3-pentanone (312538-65-1) → {(R)-2-[(4R,5S,6S)-6-((R)-1-Azido-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propoxy}-tert-butyl-diphenyl-silane (639006-74-9)

Guidance literature:

Multi-step reaction with 6 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

With titanium(IV) isopropylate; sodium azide; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In phosphate buffer; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol035874f

upstream raw materials:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

(S)-2-p-Methoxybenzyloxy-3-pentanone

(2S,4S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-hydroxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-heptanone

(2R,3R,4S,5S,6S)-1-tert-butyldiphenylsilyloxy-6-(4-methoxybenzyloxy)-2,4-dimethyl-3,5-heptanediol

Downstream raw materials:

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

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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