(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

Base Information

• Chemical Name: (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
• CAS No.: 855855-62-8
• Molecular Formula: C₂₆H₄₄O₄Si
• Molecular Weight: 448.718

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 19 articles about (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 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: 86.0%

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) → (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 (855855-62-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

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)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-((4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-hex-4-en-1-ol (855855-62-8)

Guidance literature:

Multi-step reaction with 12 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

12.1: 86 percent / DDQ / CH₂Cl₂; H₂O

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; 5.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.04.031

Reference yield:

O1,O2-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose (4613-68-7,14260-67-4,22248-90-4,74996-06-8) → (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 (855855-62-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 67 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

2.1: 98 percent / H₂ / Raney-Ni / ethanol / 3102.89 Torr

3.1: 72 percent / aq. AcOH / Heating

4.1: 92 percent / LiAlH₄ / tetrahydrofuran / 20 °C

5.1: 85 percent / CSA

6.1: 91 percent / DEAD; TPP / tetrahydrofuran

7.1: 74 percent / PTSA / methanol

8.1: 89 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

9.1: 94 percent / NaH / tetrahydrofuran / 0 °C

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

10.2: 85 percent / tetrahydrofuran

11.1: 73 percent / red-Al(R) / diethyl ether / -20 °C

12.1: 95 percent / CSA / acetone

13.1: 86 percent / DDQ / CH₂Cl₂; H₂O

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; 1.1: Wittig olefination / 6.1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2005.04.031

upstream 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

(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:

(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

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