((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane
• CAS No.: 753016-46-5
• Molecular Formula: C₃₈H₆₀O₆Si
• Molecular Weight: 640.976
• Mol file: 753016-46-5.mol

Synonyms:((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane

There total 21 articles about ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-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: 94.0%

t-butyldimethylsiyl triflate (69739-34-0) + (E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol (753016-65-8) → ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane (753016-46-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/ol049219z

Reference yield:

(E)-(3'-bromo-but-2'-enyloxymethyl)-benzene (157733-27-2) → ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane (753016-46-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 68 percent / PdCl₂[P(o-Tol)3]2 / tetrahydrofuran / 96 h / 20 °C

2.1: 96 percent / DIBAL / CH₂Cl₂; hexane / -78 - 45 °C

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

4.1: Sn(OTf)2; Et₃N / CH₂Cl₂ / 3 h / -78 °C

4.2: 77 percent / CH₂Cl₂ / 6 h / -78 °C

5.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.25 h / 20 °C

5.2: 73 percent / NaBH₄ / tetrahydrofuran; methanol / 48 h / -78 °C

6.1: 92 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 86 percent / PPTS / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.2: Paterson's stereoselective aldol reaction;

DOI:10.1021/ol049219z

Reference yield:

(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-en-1-ol (753016-63-6) → ((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane (753016-46-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / Sn(OTf)2; triethylamine

2: Et₂BOMe; NaBH₄

3: TBAF / tetrahydrofuran

4: PPTS

5: 2,6-lutidine

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; 1: Swern oxidation;

DOI:10.1016/j.tetlet.2005.07.029

upstream raw materials:

t-butyldimethylsiyl triflate

(E)-(2S,3R,4S)-8-Benzyloxy-2-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,6-dimethyl-oct-6-en-3-ol

2-hydroxymethyl-1-(4-methoxybenzyloxy)-3-pentanone

(R)-2-hydroxymethyl-1-(4-methoxybenzyloxy)-3-pentanone

Downstream raw materials:

(-)-kazusamycin A

{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-methanol