(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

Base Information

Chemical Name:(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol
CAS No.:116726-61-5
Molecular Formula:C₃₁H₄₄O₅Si
Molecular Weight:524.773
Hs Code.:

Synonyms:(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

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Chemical Property of (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

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Technology Process of (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

There total 9 articles about (Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-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:

: 35784-67-9
1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

: 116726-61-5
(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) KH / 1.) THF, RT, 1 h, 2.) reflux, 8 h

2: 90 percent / 90percent AcOH / 4 h / 60 °C

3: 100 percent / Celite, Pb(AcO)4 / benzene / 0.5 h / Ambient temperature

4: 88 percent / tetrahydrofuran / 3 h

5: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

6: 79 percent / DIBAL / toluene / 1 h / -78 °C

7: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

With lead(IV) acetate; Celite; hydrogen; tert.-butyl lithium; potassium hydride; diisobutylaluminium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene; benzene;
DOI:10.1021/jo00260a016

Reference yield:

: (S)-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-acetaldehyde

: 116726-61-5
(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / tetrahydrofuran / 3 h

2: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

3: 79 percent / DIBAL / toluene / 1 h / -78 °C

4: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

With hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jo00260a016

Reference yield:

: 116726-53-5
tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

: 116726-61-5
(Z)-6-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-methyl-hex-3-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / 90percent AcOH / 4 h / 60 °C

2: 100 percent / Celite, Pb(AcO)4 / benzene / 0.5 h / Ambient temperature

3: 88 percent / tetrahydrofuran / 3 h

4: 96 percent / H₂ / 5percent Pd/C / methanol / 3 h

5: 79 percent / DIBAL / toluene / 1 h / -78 °C

6: 1.) tert-BuLi / 1.) pentane, ether, -65 deg C, 30 min, 2.) 30 min

With lead(IV) acetate; Celite; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; toluene; benzene;
DOI:10.1021/jo00260a016