(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

Base Information

Chemical Name:(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid
CAS No.:925458-13-5
Molecular Formula:C₃₁H₄₄O₅Si
Molecular Weight:524.773
Hs Code.:

Synonyms:(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

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Chemical Property of (Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

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Technology Process of (Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

There total 22 articles about (Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid 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%

: 925458-12-4
(Z)-methyl 3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)hept-1-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate

: 925458-13-5
(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

Guidance literature:: With lithium hydroxide; water; In methanol; at 20 ℃; for 24h;
DOI:10.1055/s-2006-950317

Reference yield: 72.0%

: (Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolan-4-yl}prop-2-en-1-ol

: 925458-13-5
(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 0 - 20 ℃; for 1h;
DOI:10.1002/ejoc.201300022

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 925458-13-5
(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / imidazole; DMAP / dimethylformamide / 2 h / 0 °C

2: 91 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -65 °C

4: tetrahydrofuran / 6 h / Heating

5: 94 percent / K₂CO₃; K₃Fe(CN)6; MeSO₂NH₂ / (DHQ)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6: 89 percent / p-TSA / CH₂Cl₂ / 2 h

7: 85 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

8: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -65 °C

9: methanol / 24 h / -78 °C

10: LiOH / methanol; H₂O / 0 - 20 °C

With 1H-imidazole; dmap; lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Swern oxidation / 4: Wittig reaction / 5: Sharpless asymmetric dihydroxylation / 8: Swern oxidation / 9: Wittig reaction;
DOI:10.1016/j.tetlet.2005.07.153