(E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol

Base Information

• Chemical Name: (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol
• CAS No.: 855855-59-3
• Molecular Formula: C₃₁H₄₈O₅Si
• Molecular Weight: 528.805
• Mol file: 855855-59-3.mol

Synonyms:(E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol

Chemical Property of (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol

There total 16 articles about (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol 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: 73.0%

Benzoic acid (1S,3S,7R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9-(4-methoxy-benzyloxy)-1-phenethyl-non-5-ynyl ester (855855-51-5) → (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol (855855-59-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at -20 ℃;

DOI:10.1016/j.tetlet.2005.04.031

Reference yield:

(3aR,5S,6aR)-2,2-Dimethyl-5-((E)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole (855855-55-9) → (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol (855855-59-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / H₂ / Raney-Ni / ethanol / 3102.89 Torr

2.1: 72 percent / aq. AcOH / Heating

3.1: 92 percent / LiAlH₄ / tetrahydrofuran / 20 °C

4.1: 85 percent / CSA

5.1: 91 percent / DEAD; TPP / tetrahydrofuran

6.1: 74 percent / PTSA / methanol

7.1: 89 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

8.1: 94 percent / NaH / tetrahydrofuran / 0 °C

9.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 °C

9.2: 85 percent / tetrahydrofuran

10.1: 73 percent / red-Al(R) / diethyl ether / -20 °C

With lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; thiamine diphosphate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 5.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.04.031

Reference yield:

3-deoxy-1,2-O-isopropylidene-D-glucose (4005-46-3,4494-96-6,22248-87-9,142941-40-0) → (E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol (855855-59-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 96 percent / NaIO₄ on silica gel / CH₂Cl₂

2.1: 67 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

3.1: 98 percent / H₂ / Raney-Ni / ethanol / 3102.89 Torr

4.1: 72 percent / aq. AcOH / Heating

5.1: 92 percent / LiAlH₄ / tetrahydrofuran / 20 °C

6.1: 85 percent / CSA

7.1: 91 percent / DEAD; TPP / tetrahydrofuran

8.1: 74 percent / PTSA / methanol

9.1: 89 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

10.1: 94 percent / NaH / tetrahydrofuran / 0 °C

11.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / -78 °C

11.2: 85 percent / tetrahydrofuran

12.1: 73 percent / red-Al(R) / diethyl ether / -20 °C

With sodium periodate; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; thiamine diphosphate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 2.1: Wittig olefination / 7.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.04.031

upstream raw materials:

Benzoic acid (1S,3S,7R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9-(4-methoxy-benzyloxy)-1-phenethyl-non-5-ynyl ester

(3aR,5S,6aR)-2,2-Dimethyl-5-((E)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole

(2R,4R)-6-Phenyl-hexane-1,2,4-triol

(2S,3R,5R)-5-Phenethyl-tetrahydro-furan-2,3-diol

Downstream raw materials:

tert-Butyl-{(E)-(R)-4-((4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-1-[2-(4-methoxy-benzyloxy)-ethyl]-but-2-enyloxy}-dimethyl-silane

(E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-((4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-hex-4-en-1-ol

(2Z,6E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-((4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-octa-2,6-dienoic acid ethyl ester