{(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

Base Information

• Chemical Name: {(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
• CAS No.: 753016-66-9
• Molecular Formula: C₃₀H₅₂O₅Si
• Molecular Weight: 520.825
• Mol file: 753016-66-9.mol

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 23 articles about {(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 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: 68.0%

((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) → {(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 (753016-66-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; at 0 ℃; for 6h; pH=7;

DOI:10.1021/ol049219z

Reference yield:

(E)-(3'-bromo-but-2'-enyloxymethyl)-benzene (157733-27-2) → {(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 (753016-66-9)

Guidance literature:

Multi-step reaction with 9 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

9.1: 68 percent / DDQ / CH₂Cl₂; aq. phosphate buffer / 6 h / 0 °C / pH 7

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; phosphate buffer; 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) → {(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 (753016-66-9)

Guidance literature:

Multi-step reaction with 7 steps

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

2: Et₂BOMe; NaBH₄

3: TBAF / tetrahydrofuran

4: PPTS

5: 2,6-lutidine

6: 65 percent / DDQ

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1: Swern oxidation;

DOI:10.1016/j.tetlet.2005.07.029

upstream raw materials:

((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

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

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

1-benzyloxy-2-(benzyloxymethyl)-3-pentanol

Downstream raw materials:

(E)-3-{(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}-2-methyl-prop-2-en-1-ol

(E)-3-{(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}-2-methyl-acrylic acid ethyl ester

(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-5-((E)-2-methyl-3-triisopropylsilanyloxy-propenyl)-[1,3]dioxane

(-)-kazusamycin A