(2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

Base Information

• Chemical Name: (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether
• CAS No.: 162466-15-1
• Molecular Formula: C₂₈H₃₄O₃Si
• Molecular Weight: 446.662

Synonyms:(2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

Chemical Property of (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

There total 10 articles about (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether 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: 91.0%

2,2-dimethoxy-propane (77-76-9) + (2S,3R)-2,3-dihydroxy-3-phenylpropanyl tert-butyldiphenylsilyl ether (162466-14-0) → (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether (162466-15-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1016/0040-4020(94)01025-U

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether (162466-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (+)-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide

1.2: triethylamine; 4-(dimethylamino)pyridine

1.3: p-toluenesulfonic acid / tetrahydrofuran; H₂O

2.1: p-toluenesulfonic acid / acetone / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; In acetone;

DOI:10.1246/bcsj.80.387

Reference yield:

2,2-dimethoxy-propane (77-76-9) + tert-butylchlorodiphenylsilane (58479-61-1) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → 4-(t-butyldiphenylsilyloxy)methyl-2,2-dimethyl-5-phenyl-1,3-dioxolane (936210-31-0) + 4-(t-butyldiphenylsilyloxy)methyl-2,2-dimethyl-5-phenyl-1,3-dioxolane + 4-(t-butyldiphenylsilyloxy)methyl-2,2-dimethyl-5-phenyl-1,3-dioxolane + (2S,3R)-2,3-isopropylidenyloxy-3-phenylpropanyl tert-butyldiphenylsilyl ether (162466-15-1)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts.;

DOI:10.1246/bcsj.80.387

upstream raw materials:

2,2-dimethoxy-propane

(2S,3R)-2,3-dihydroxy-3-phenylpropanyl tert-butyldiphenylsilyl ether

tert-butylchlorodiphenylsilane

(2E)-3-phenyl-2-propen-1-ol

Downstream raw materials:

(+)-goniofufurone

(5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one

(6R,7R,8R)-goniodiol-8-monoacetate

(R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3,6-dihydro-pyran-2-one

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