tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane
• CAS No.: 177471-62-4
• Molecular Formula: C₃₀H₃₆O₄Si
• Molecular Weight: 488.699

Synonyms:tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane

Chemical Property of tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane

Chemical Property:

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Technology Process of tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane

There total 9 articles about tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane 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: 70.0%

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose (174590-90-0) → tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane (177471-62-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - -40 ℃; for 0.666667h; Inert atmosphere;

Reference yield: 51.0%

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose (174590-90-0) → ((3aR,4R,6aS)-2,2-Dimethyl-6-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol + tert-butyl(((3aR,4R,6R,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane + tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane (177471-62-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -40 ℃; for 1h;

DOI:10.1021/jo960091b

Reference yield: 31.0%

(((3aR,4R,6R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(tert-butyl)diphenylsilane + phenylmagnesium bromide (100-58-3) → tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane (177471-62-4)

Guidance literature:

With triphenylphosphine; In diethyl ether; at 0 - 20 ℃; diastereoselective reaction;

DOI:10.1016/j.tetlet.2013.12.035

upstream raw materials:

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

phenyllithium

phenylmagnesium bromide

Downstream raw materials:

(-)-1'-deoxy-1'-phenyl-β-D-ribofuranose

(1S,2R,3S,4R)-1-deoxy-3,5-O-(1,3-disiloxanediyl-1,1,3,3-tetraisopropyl)-1-phenylribose

(1S,2R,3S,4R)-1-deoxy-3,5-O-(1,3-disiloxanediyl-1,1,3,3-tetraisopropyl)-2-O-methyl-1-phenylribose

(1S,2R,3S,4R)-1-deoxy-2-O-methyl-1-phenylribose

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