(2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol

Base Information

• Chemical Name: (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol
• CAS No.: 1392284-89-7
• Molecular Formula: C₃₄H₅₇NO₇Si
• Molecular Weight: 619.915
• Mol file: 1392284-89-7.mol

Synonyms:(2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol

Chemical Property of (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol

There total 46 articles about (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol 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: 80.0%

(2S,6S,7S)-2-[(tert-Butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-one (1392284-92-2) → (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol (1392284-89-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -90 ℃; for 0.75h; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0033-1338493

Reference yield: 80.0%

C33H55NO7Si (1392284-88-6) + methyl iodide (74-88-4) → (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol (1392284-89-7) + C34H57NO7Si (1401008-50-1)

Guidance literature:

C₃₃H₅₅NO₇Si; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

methyl iodide; In tetrahydrofuran; at 10 ℃; for 1.08333h;

DOI:10.1055/s-0033-1338493

Reference yield:

(S)-tert-butyl(1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-yloxy)dimethylsilane (1414941-22-2) → (2S,4S,6S,7S)-2-[(tert-butyldimethylsilyl)oxy]-6-methoxy-8-[(4-methoxybenzyl)oxy]-1-{4-[(S)-1-methoxybut-3-en-1-yl]oxazol-2-yl}-3,3,7-trimethyloctan-4-ol (1392284-89-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: ozone; triphenylphosphine / dichloromethane / -78 - 20 °C

2.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 1.5 h / 20 °C / Inert atmosphere

3.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -30 - 20 °C / Inert atmosphere

4.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; Bromotrichloromethane / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

7.1: diethyl ether / 2 h / -100 °C / Inert atmosphere

7.2: 20 °C

8.1: silver(l) oxide / diethyl ether / 18 h / 20 °C / Molecular sieve; Darkness

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.42 h / 20 °C / Inert atmosphere

10.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

11.2: 0.67 h / -40 °C

12.1: triethylamine; dicyclohexylboron chloride / diethyl ether; tetrahydrofuran / 1.5 h / -30 °C

12.2: 1.5 h / -78 °C

12.3: 2 h / 0 - 20 °C

13.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C

13.2: 0.67 h / 0 °C

14.1: pyridinium chlorochromate / dichloromethane / 1.5 h / Reflux

15.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.75 h / -90 °C / Inert atmosphere

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; Bromotrichloromethane; diethylamino-sulfur trifluoride; dicyclohexylboron chloride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; lithium hexamethyldisilazane; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; dichloromethane; water; mineral oil; tert-butyl alcohol;

DOI:10.1055/s-0033-1338493

upstream raw materials:

C₃₃H₅₅NO₇Si

methyl iodide

(S)-tert-butyl(1-(4-methoxybenzyloxy)-2,2-dimethylhex-5-en-3-yloxy)dimethylsilane

(S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethylpentanoic acid

Downstream raw materials:

C₄₀H₆₈BNO₉Si

C₄₀H₆₈BNO₉Si

C₄₈H₈₂INO₁₀Si₂