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

Base Information

• Chemical Name: 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
• CAS No.: 855855-61-7
• Molecular Formula: C₃₄H₅₂O₅Si
• Molecular Weight: 568.869
• Mol file: 855855-61-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 17 articles about 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 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: 95.0%

(E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol (855855-59-3) + 2,2-dimethoxy-propane (77-76-9) → 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 (855855-61-7)

Guidance literature:

With camphor-10-sulfonic acid; In acetone;

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) → 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 (855855-61-7)

Guidance literature:

Multi-step reaction with 11 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

11.1: 95 percent / CSA / acetone

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; acetone; 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) → 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 (855855-61-7)

Guidance literature:

Multi-step reaction with 13 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

13.1: 95 percent / CSA / acetone

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; acetone; 2.1: Wittig olefination / 7.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.04.031

upstream raw materials:

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

2,2-dimethoxy-propane

(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

Downstream raw materials:

(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