(E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol

Base Information

• Chemical Name: (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol
• CAS No.: 1352739-63-9
• Molecular Formula: C₃₆H₆₃NO₆SSi₂
• Molecular Weight: 694.136

Synonyms:(E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol

Chemical Property of (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol

There total 11 articles about (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-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: 28.0%

tert-butyl (E)-6-[(tert-butyldimethylsilyl)oxy]-7-{4-[2-(tert-butyldimethylsilyloxy)ethyl]thiazol-2-yl}-2-hydroxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-7-methyloct-3-enoate (1352739-53-7) → (E)-6-[(tert-butyldimethylsilyl)oxy]-7-(4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-2-yl)-2-hydroxy-2-{2-[(4-methoxybenzyl)-oxy]ethyl}-7-methyloct-3-enal (1352739-61-7) + (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol (1352739-63-9)

Guidance literature:

tert-butyl (E)-6-[(tert-butyldimethylsilyl)oxy]-7-{4-[2-(tert-butyldimethylsilyloxy)ethyl]thiazol-2-yl}-2-hydroxy-2-{2-[(4-methoxybenzyl)oxy]ethyl}-7-methyloct-3-enoate; With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; Inert atmosphere;

With water; In diethyl ether; Inert atmosphere;

DOI:10.1002/ejoc.201100669

Reference yield:

4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole (292073-56-4) → (E)-6-[(tert-butyldimethylsilyl)oxy]-7-(4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-2-yl)-2-hydroxy-2-{2-[(4-methoxybenzyl)-oxy]ethyl}-7-methyloct-3-enal (1352739-61-7) + (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol (1352739-63-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere

3.1: methanol; chloro-trimethyl-silane / 15 h / 50 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: ammonium chloride; zinc / tetrahydrofuran; water / 48 h / 20 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 1 h / Inert atmosphere

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

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

9.2: Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

11.1: n-butyllithium / diethyl ether; n-heptane / 1 h / -78 °C / Inert atmosphere

11.2: 1.5 h / -78 °C / Inert atmosphere

11.3: Inert atmosphere

12.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Inert atmosphere

12.2: Inert atmosphere

With 2,6-dimethylpyridine; chromium dichloride; methanol; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; ammonium chloride; Dess-Martin periodane; triethylamine; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; n-heptane; dichloromethane; water; dimethyl sulfoxide; 4.1: Dess-Martin oxidation / 5.1: Barbier reaction;

DOI:10.1002/ejoc.201100669

Reference yield:

C10H13NO3S (1364099-45-5) → (E)-6-[(tert-butyldimethylsilyl)oxy]-7-(4-{2-[(tert-butyldimethylsilyl)oxy]ethyl}thiazol-2-yl)-2-hydroxy-2-{2-[(4-methoxybenzyl)-oxy]ethyl}-7-methyloct-3-enal (1352739-61-7) + (E)-6-((tert-butyldimethylsilyl)oxy)-7-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)thiazol-2-yl)-2-(2-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-3-ene-1,2-diol (1352739-63-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ammonium chloride; zinc / tetrahydrofuran; water / 48 h / 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

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

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

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

5.2: Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

7.1: n-butyllithium / diethyl ether; n-heptane / 1 h / -78 °C / Inert atmosphere

7.2: 1.5 h / -78 °C / Inert atmosphere

7.3: Inert atmosphere

8.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Inert atmosphere

8.2: Inert atmosphere

With 2,6-dimethylpyridine; chromium dichloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; ammonium chloride; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; n-heptane; dichloromethane; water; 1.1: Barbier 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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