benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester
• CAS No.: 835913-60-5
• Molecular Formula: C₂₃H₃₉NO₄Si
• Molecular Weight: 421.652

Synonyms:benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester

Chemical Property of benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester

There total 2 articles about benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester 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: 75.0%

tert-butyldimethylsilyl chloride (18162-48-6) + Benzyl-[(S)-1-((S)-1,2-dihydroxy-ethyl)-allyl]-carbamic acid tert-butyl ester (835913-59-2) → benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester (835913-60-5)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 8h;

DOI:10.1016/j.tetlet.2004.11.033

Reference yield:

(3S,4S)-N-benzyl-N-(tert-butoxycarbonyl)-4,5-O-isopropylidene-4,5-dihydroxypent-1-en-3-amine (194422-04-3) → benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester (835913-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / aq. AcOH / 12 h / 20 °C

2: 75 percent / imidazole / CH₂Cl₂ / 8 h / 0 - 20 °C

With 1H-imidazole; acetic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2004.11.033

Reference yield: 82.0%

methyl iodide (74-88-4) + benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-allyl}-carbamic acid tert-butyl ester (835913-60-5) → benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-ethyl]-allyl}-carbamic acid tert-butyl ester (835913-61-6)

Guidance literature:

With silver(l) oxide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2004.11.033

upstream raw materials:

tert-butyldimethylsilyl chloride

Benzyl-[(S)-1-((S)-1,2-dihydroxy-ethyl)-allyl]-carbamic acid tert-butyl ester

(3S,4S)-N-benzyl-N-(tert-butoxycarbonyl)-4,5-O-isopropylidene-4,5-dihydroxypent-1-en-3-amine

Downstream raw materials:

benzyl-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-ethyl]-allyl}-carbamic acid tert-butyl ester

(2S,3S)-2-(Benzyl-methyl-amino)-3-methoxy-butane-1,4-diol

Benzyl-[(S)-1-((S)-2-hydroxy-1-methoxy-ethyl)-allyl]-carbamic acid tert-butyl ester

Benzyl-((1S,2S)-3-hydroxy-1-hydroxymethyl-2-methoxy-propyl)-carbamic acid tert-butyl ester

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