(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

Base Information

Chemical Name:(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester
CAS No.:620116-54-3
Molecular Formula:C₂₄H₂₆O₅Si
Molecular Weight:422.553
Hs Code.:

Synonyms:(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

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Chemical Property of (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

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Technology Process of (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

There total 4 articles about (5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester 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: 79.0%

: 620116-53-2
(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-formyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

: 620116-54-3
(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

Guidance literature:: With tri-n-butyl-tin hydride; silica gel; In toluene; at 80 ℃; for 10h;
DOI:10.1021/ja0376588

Reference yield:

: 3839-31-4
dimethyl(phenyl)silyllithium

: 620116-54-3
(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 3 h / -78 °C

1.2: tetrahydrofuran / -78 - 25 °C

1.3: 202.6 mg / aq. KHCO₃; aq. K₂CO₃ / methanol / 55 h / 25 °C

2.1: MeOTf / CH₂Cl₂ / 2 h / 25 °C

2.2: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 25 °C

2.3: 100 percent / (CO₂H)2*H₂O / tetrahydrofuran; H₂O / 16 h / 25 °C

3.1: 79 percent / Bu₃SnH; SiO₂ / toluene / 10 h / 80 °C

With tri-n-butyl-tin hydride; silica gel; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja0376588

Reference yield:

: 4-isopropyl-2-naphtho[2,3-d][1,3]dioxol-6-yl-4,5-dihydro-oxazole

: 620116-54-3
(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 3 h / -78 °C

1.2: tetrahydrofuran / -78 - 25 °C

1.3: 202.6 mg / aq. KHCO₃; aq. K₂CO₃ / methanol / 55 h / 25 °C

2.1: MeOTf / CH₂Cl₂ / 2 h / 25 °C

2.2: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 25 °C

2.3: 100 percent / (CO₂H)2*H₂O / tetrahydrofuran; H₂O / 16 h / 25 °C

3.1: 79 percent / Bu₃SnH; SiO₂ / toluene / 10 h / 80 °C

With tri-n-butyl-tin hydride; silica gel; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja0376588