tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate

Base Information

• Chemical Name: tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate
• CAS No.: 1352739-59-3
• Molecular Formula: C₄₀H₆₉NO₇SSi₂
• Molecular Weight: 764.227

Synonyms:tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate

Chemical Property of tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate

Chemical Property:

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Technology Process of tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate

There total 19 articles about tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate 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: 61.0%

(E)-2-{3-[(tert-butyldimethylsilyl)oxy]-6-iodo-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazole (1352739-48-0) + tert-butyl 4-[(4-methoxybenzyl)oxy]-2-oxobutanoate (512196-61-1) → tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate (1352739-59-3)

Guidance literature:

(E)-2-{3-[(tert-butyldimethylsilyl)oxy]-6-iodo-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazole; With n-butyllithium; In tetrahydrofuran; n-heptane; at -78 ℃; for 1h; Inert atmosphere;

tert-butyl 4-[(4-methoxybenzyl)oxy]-2-oxobutanoate; In tetrahydrofuran; n-heptane; at -78 ℃; for 1.5h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; n-heptane; water; Inert atmosphere;

DOI:10.1002/ejoc.201100669

Reference yield:

methyl 2-[2-(3-hydroxy-2-methylhex-5-en-2-yl)thiazol-4-yl]acetate (1352739-32-2) → tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate (1352739-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 1 h / Inert atmosphere

3.1: chromium dichloride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; n-heptane / 1 h / -78 °C / Inert atmosphere

6.2: 1.5 h / -78 °C / Inert atmosphere

6.3: Inert atmosphere

With 2,6-dimethylpyridine; chromium dichloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; 1,4-dioxane; diethyl ether; n-heptane; dichloromethane; water;

DOI:10.1002/ejoc.201100669

Reference yield:

4-[(4-methoxybenzyl)oxy]-2-methylenebutanal (1352739-49-1) → tert-butyl 2-(2-{3-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-2-yl}-4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-5-yl)-2-hydroxy-4-[(4-methoxybenzyl)oxy]butanoate (1352739-59-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; acetic acid; tert-butyl alcohol / 4 h / 20 °C / Inert atmosphere

2.1: dmap / tert-butyl alcohol / 8 h / 20 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 12 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; n-heptane / 1 h / -78 °C / Inert atmosphere

4.2: 1.5 h / -78 °C / Inert atmosphere

4.3: Inert atmosphere

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; In tetrahydrofuran; 1,4-dioxane; n-heptane; water; acetic acid; tert-butyl alcohol; 1.1: Pinnick reaction;

DOI:10.1002/ejoc.201100669

upstream raw materials:

C₁₀H₁₃NO₃S

methyl 2-[2-(3-hydroxy-2-methylhex-5-en-2-yl)thiazol-4-yl]acetate

2-(2-{1-[(tert-butyldiphenylsilyl)oxy]-2-methylpropan-2-yl}thiazol-4-yl)acetonitrile

methyl 2-[2-(1-hydroxy-2-methylpropan-2-yl)thiazol-4-yl]acetate

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