(1S^*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane

Base Information

• Chemical Name: (1S^*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane
• CAS No.: 77773-88-7
• Molecular Formula: C₂₀H₃₁BO₃Si
• Molecular Weight: 358.361

Synonyms:(1S^*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane

Chemical Property of (1S^*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane

Chemical Property:

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Technology Process of (1S^*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane

There total 3 articles about (1S^*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane 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: 93.0%

(1S*,5R,9R)-9-Hydroxy-3-phenyl-2,4-dioxa-3-boratricyclo<5.3.1.05,10>undecane (77773-87-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (1S*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.05,10>undecane (77773-88-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1021/jo00328a038

Reference yield:

Bicyclo<2.2.2>octane-2,6,7-trione (36520-55-5) → (1S*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.05,10>undecane (77773-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / 1.) dioxane, THF, 2.) MeOH, H₂O, 2 deg C

2: 93 percent / imidazole / dimethylformamide / 2 h / 100 °C

With 1H-imidazole; lithium aluminium tetrahydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00328a038

Reference yield:

phenylboronic acid (98-80-6) → (1S*,5R,9R)-3-Phenyl-9-<(tert-butyldimethylsilyl)oxy>-2,4-dioxa-3-boratricyclo<5.3.1.05,10>undecane (77773-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / 1.) dioxane, THF, 2.) MeOH, H₂O, 2 deg C

2: 93 percent / imidazole / dimethylformamide / 2 h / 100 °C

With 1H-imidazole; lithium aluminium tetrahydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00328a038

upstream raw materials:

(1S^*,5R,9R)-9-Hydroxy-3-phenyl-2,4-dioxa-3-boratricyclo<5.3.1.0^5,10>undecane

tert-butyldimethylsilyl chloride

Bicyclo<2.2.2>octane-2,6,7-trione

phenylboronic acid

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