(R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol

Base Information

Chemical Name:(R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol
CAS No.:154912-77-3
Molecular Formula:C₁₉H₃₀O₄
Molecular Weight:322.445
Hs Code.:

Synonyms:

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Chemical Property of (R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol

Chemical Property:

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Technology Process of (R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol

There total 12 articles about (R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol 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:

: 96154-47-1
(R)-2-methyl-1,4-butanediol 4-benzyl ether

: 154912-77-3
(R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: imidazole / dimethylformamide / 0 °C

2: H₂ / 10 percent Pd-C / methanol / Ambient temperature

3: TEA, DCM / 0 °C

4: LiBr, NaHCO₃ / tetrahydrofuran / Ambient temperature

5: 60 percent / 1.) LiNH₂ / liquid ammonia / -33 °C / 1.) 2 h, 2.) 16 h

6: 95 percent / H₂, quinoline / Lindlar's catalyst / methanol

7: (-)-DIPT, TBHP, Ti(O-i-Pr)4, 3 Angstroem molecular sieves, DCM

8: 75 percent / Red-Al / tetrahydrofuran / Ambient temperature

9: Bu₄NF / tetrahydrofuran / Ambient temperature

10: PTSA

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium amide; 3 A molecular sieve; TEA; tetrabutyl ammonium fluoride; hydrogen; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium bromide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; ammonia; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61612-X

Reference yield:

: 91550-14-0
(2R)-4-(Benzyloxy)-2-methyl-1-butanal

: 154912-77-3
(R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: NaBH₄ / methanol / 0 °C

2: imidazole / dimethylformamide / 0 °C

3: H₂ / 10 percent Pd-C / methanol / Ambient temperature

4: TEA, DCM / 0 °C

5: LiBr, NaHCO₃ / tetrahydrofuran / Ambient temperature

6: 60 percent / 1.) LiNH₂ / liquid ammonia / -33 °C / 1.) 2 h, 2.) 16 h

7: 95 percent / H₂, quinoline / Lindlar's catalyst / methanol

8: (-)-DIPT, TBHP, Ti(O-i-Pr)4, 3 Angstroem molecular sieves, DCM

9: 75 percent / Red-Al / tetrahydrofuran / Ambient temperature

10: Bu₄NF / tetrahydrofuran / Ambient temperature

11: PTSA

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium amide; 3 A molecular sieve; TEA; tetrabutyl ammonium fluoride; hydrogen; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium bromide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; ammonia; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61612-X

Reference yield:

: 154912-68-2
(2R,3R)-5-benzyloxy-3-methylpentane-1,2-diol

: 154912-77-3
(R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1: NaIO₄ / tetrahydrofuran; H₂O / 0 °C

2: NaBH₄ / methanol / 0 °C

3: imidazole / dimethylformamide / 0 °C

4: H₂ / 10 percent Pd-C / methanol / Ambient temperature

5: TEA, DCM / 0 °C

6: LiBr, NaHCO₃ / tetrahydrofuran / Ambient temperature

7: 60 percent / 1.) LiNH₂ / liquid ammonia / -33 °C / 1.) 2 h, 2.) 16 h

8: 95 percent / H₂, quinoline / Lindlar's catalyst / methanol

9: (-)-DIPT, TBHP, Ti(O-i-Pr)4, 3 Angstroem molecular sieves, DCM

10: 75 percent / Red-Al / tetrahydrofuran / Ambient temperature

11: Bu₄NF / tetrahydrofuran / Ambient temperature

12: PTSA

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; lithium amide; 3 A molecular sieve; TEA; tetrabutyl ammonium fluoride; hydrogen; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium bromide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; ammonia; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61612-X