3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

Base Information

Chemical Name:3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate
CAS No.:864948-10-7
Molecular Formula:C₁₉H₂₈O₄S
Molecular Weight:352.495
Hs Code.:

Synonyms:3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

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Chemical Property of 3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

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Technology Process of 3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

There total 8 articles about 3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate 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: 82.0%

: 864948-09-4
3-[(4R)-5-(acetyloxy)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl pivalate

: 108-98-5
thiophenol

: 864948-10-7
3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

: 3-[(4R,5S)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 - -40 ℃;
DOI:10.1021/jo050888f

Reference yield:

: 3282-30-2
pivaloyl chloride

: 864948-10-7
3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

Guidance literature:: Multi-step reaction with 8 steps

1: 52 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 4 h / 20 °C

2: 95 percent / molecular sieves 4 Angstroem; florisil; sodium acetate / Celite; pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / acetonitrile / 1 h / 65 °C

4: 90 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 6 h / 0 °C

5: 97 percent / camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

6: 98 percent / KOH / tetrahydrofuran; H₂O / pH 11

7: 88 percent / iodine / CH₂Cl₂ / 4 h

8: 82 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - -40 °C

With pyridine; dmap; potassium hydroxide; florisil; methanesulfonamide; 4 A molecular sieve; AD-mix-β; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; sodium acetate; Celite; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo050888f

Reference yield:

: 209254-60-4
4-pivaloyloxy-1-butanol

: 864948-10-7
3-[(4R,5R)-2,2-dimethyl-5-(phenylthio)-1,3-dioxolan-4-yl]propyl pivalate

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / molecular sieves 4 Angstroem; florisil; sodium acetate / Celite; pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

2: 93 percent / acetonitrile / 1 h / 65 °C

3: 90 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 6 h / 0 °C

4: 97 percent / camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

5: 98 percent / KOH / tetrahydrofuran; H₂O / pH 11

6: 88 percent / iodine / CH₂Cl₂ / 4 h

7: 82 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - -40 °C

With potassium hydroxide; florisil; methanesulfonamide; 4 A molecular sieve; AD-mix-β; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; sodium acetate; Celite; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo050888f