Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester
CAS No.:476005-17-1
Molecular Formula:C₂₄H₄₀O₆Si
Molecular Weight:452.663
Hs Code.:

Synonyms:Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

There total 5 articles about Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl 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: 68.0%

: 476005-18-2
Benzoic acid (2R,4R,6S)-2-allyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

: 476005-17-1
Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

: Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((R)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With sulfamic acid methyl ester; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); In water; tert-butyl alcohol; at 20 ℃; for 13h;
DOI:10.1016/S0040-4020(02)00635-X

Reference yield:

: 476005-12-6
(E)-(S)-5-(2-Bromo-2-methyl-propionyloxy)-6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid ethyl ester

: 476005-17-1
Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

1.2: dimethyl sulfide / CH₂Cl₂ / 2.5 h / -78 - 20 °C

2.1: 521.7 mg / samarium diiodide / tetrahydrofuran / 0.17 h / 0 °C

3.1: 322.4 mg / DIBAH / CH₂Cl₂; hexane / 0.08 h / -78 °C

4.1: 532.6 mg / pyridine / 11 h / 20 °C

5.1: 91 percent / BF₃*Et₂O; TMSOTf / acetonitrile / 24 h / 20 °C

6.1: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 68 percent / K₃Fe(CN)6; MeSO₃NH₂; K₂CO₃ / OsO₄; (DHQ)2PYR / 2-methyl-propan-2-ol; H₂O / 13 h / 20 °C

With pyridine; 1H-imidazole; samarium diiodide; sulfamic acid methyl ester; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; potassium carbonate; ozone; potassium hexacyanoferrate(III); osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2.1: Reformatsky reaction / 7.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/S0040-4020(02)00635-X

Reference yield:

: 476005-14-8
C₂₈H₃₈O₆Si

: 476005-17-1
Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dihydroxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / BF₃*Et₂O; TMSOTf / acetonitrile / 24 h / 20 °C

2: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / 20 °C

3: 68 percent / K₃Fe(CN)6; MeSO₃NH₂; K₂CO₃ / OsO₄; (DHQ)2PYR / 2-methyl-propan-2-ol; H₂O / 13 h / 20 °C

With 1H-imidazole; sulfamic acid methyl ester; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); In dichloromethane; water; acetonitrile; tert-butyl alcohol; 3: Sharpless asymmetric dihydroxylation;
DOI:10.1016/S0040-4020(02)00635-X