[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

Base Information

Chemical Name:[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane
CAS No.:361534-84-1
Molecular Formula:C₂₇H₄₀O₆Si
Molecular Weight:488.697
Hs Code.:

[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

Synonyms:[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

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Chemical Property of [(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

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Technology Process of [(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

There total 18 articles about [(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-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:

: 1779-49-3
Methyltriphenylphosphonium bromide

: 361535-03-7
(2R,3S)-3-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-ylmethyl)-2-methyl-oxirane-2-carbaldehyde

: 361534-84-1
[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.333333h;

(2R,3S)-3-((2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-2-phenyl-6-trimethylsilanyloxy-octahydro-1,3,8,10-tetraoxa-anthracen-7-ylmethyl)-2-methyl-oxirane-2-carbaldehyde; In tetrahydrofuran; at 0 ℃; for 0.25h; Further stages.;
DOI:10.1021/ol016355k

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

: 361534-84-1
[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

Guidance literature:: Multi-step reaction with 16 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

13.1: 480 mg / DIBAH / toluene; hexane / 0.17 h / -78 °C

14.1: (+)-diethyl L-tartrate; Ti(O-i-Pr)4 / CH₂Cl₂ / 0.33 h / -20 °C

14.2: 100 percent / t-BuOOH / CH₂Cl₂ / 22 h / -20 °C

15.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.25 h / 20 °C

15.2: 56.2 mg / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

16.1: NaN(TMS)2 / tetrahydrofuran / 0.33 h / 0 °C

16.2: 42.8 mg / tetrahydrofuran / 0.25 h / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; titanium(IV) isopropylate; samarium diiodide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; 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 / 16.2: 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

: 361534-84-1
[(2S,4aS,6S,7R,8aS,9aR,10aR)-6,10a-Dimethyl-7-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-yloxy]-trimethyl-silane

Guidance literature:: Multi-step reaction with 17 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

14.1: 480 mg / DIBAH / toluene; hexane / 0.17 h / -78 °C

15.1: (+)-diethyl L-tartrate; Ti(O-i-Pr)4 / CH₂Cl₂ / 0.33 h / -20 °C

15.2: 100 percent / t-BuOOH / CH₂Cl₂ / 22 h / -20 °C

16.1: N-methylmorpholine N-oxide; molecular sieves 4 A / CH₂Cl₂ / 0.25 h / 20 °C

16.2: 56.2 mg / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

17.1: NaN(TMS)2 / tetrahydrofuran / 0.33 h / 0 °C

17.2: 42.8 mg / tetrahydrofuran / 0.25 h / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; titanium(IV) isopropylate; samarium diiodide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; 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 / 17.2: Wittig reaction;
DOI:10.1021/ol016355k