(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester
CAS No.:361535-01-5
Molecular Formula:C₂₈H₄₂O₇Si
Molecular Weight:518.723
Hs Code.:

(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

Synonyms:(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

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Chemical Property of (E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

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Technology Process of (E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

There total 14 articles about (E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester 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:

: 361534-73-8
(2S,4aS,6R,7S,8aR)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 361535-01-5
(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2.1: CH₂Cl₂ / 3 h / -78 - 0 °C

3.1: 1.33 g / molecular sieves 4 A / dimethylsulfoxide / 0.67 h / 80 °C

4.1: 87 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

5.1: 89 percent / tetrahydrofuran / 1 h / 0 - 20 °C

6.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.75 h / 20 °C

6.2: 93 percent / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 487 mg / n-Bu₄NF*xH₂O / tetrahydrofuran / 2.5 h / 20 °C

8.1: 544 mg / N-methylmorpholine / CH₂Cl₂ / 6 h / 20 °C

9.1: 99 percent / SmI₂ / methanol; tetrahydrofuran / 0.08 h / 0 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 513 mg / DIBAH / toluene; hexane / 0.25 h / -78 °C

12.1: 565 mg / toluene / 100 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 5.1: Grignard reaction / 8.1: hetero-Michael reaction / 12.1: Wittig reaction;
DOI:10.1021/ol016355k

Reference yield:

: 1053634-48-2
(2S,4R,5S)-4-((2S,3S)-3-Hydroxymethyl-3-methyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

: 361535-01-5
(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 100 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: CH₂Cl₂ / 3 h / -78 - 0 °C

4.1: 1.33 g / molecular sieves 4 A / dimethylsulfoxide / 0.67 h / 80 °C

5.1: 87 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 89 percent / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.75 h / 20 °C

7.2: 93 percent / tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 487 mg / n-Bu₄NF*xH₂O / tetrahydrofuran / 2.5 h / 20 °C

9.1: 544 mg / N-methylmorpholine / CH₂Cl₂ / 6 h / 20 °C

10.1: 99 percent / SmI₂ / methanol; tetrahydrofuran / 0.08 h / 0 °C

11.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

12.1: 513 mg / DIBAH / toluene; hexane / 0.25 h / -78 °C

13.1: 565 mg / toluene / 100 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 6.1: Grignard reaction / 9.1: hetero-Michael reaction / 13.1: Wittig reaction;
DOI:10.1021/ol016355k

Reference yield:

: 361534-95-4
1-((2S,4aS,6R,7S,8aR)-7-Hydroxy-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propan-2-one

: 361535-01-5
(E)-4-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-2-methyl-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 544 mg / N-methylmorpholine / CH₂Cl₂ / 6 h / 20 °C

2: 99 percent / SmI₂ / methanol; tetrahydrofuran / 0.08 h / 0 °C

3: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

4: 513 mg / DIBAH / toluene; hexane / 0.25 h / -78 °C

5: 565 mg / toluene / 100 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 1: hetero-Michael reaction / 5: Wittig reaction;
DOI:10.1021/ol016355k