(S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:228724-96-7
Molecular Formula:C₂₆H₃₇NO₇
Molecular Weight:475.582
Hs Code.:

(S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 18 articles about (S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

: (R)-4-[((2S,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-methylsulfanylthiocarboxyoxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 228724-96-7
(S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; Yield given;
DOI:10.1016/S0040-4039(99)00413-X

Reference yield:

: 125877-97-6
tert-Butyl-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane

: 228724-96-7
(S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) 9-BBN; 2.) H₂O₂, NaHCO₃ / 1.) THF

2: Et₃N, DMAP / CH₂Cl₂

3: n-Bu₄NF / tetrahydrofuran

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C to RT

5: L-selectride / tetrahydrofuran / -78 °C

6: imidazole, DMAP / dimethylformamide / 50 °C

7: PPTS / methanol

8: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂ / 0 °C

9: CH₂Cl₂

10: DIBAL / CH₂Cl₂ / -78 °C

11: 80 percent / t-BuOOH, Ti(O-i-Pr)4, (+)-diethyl tartrate, 4 A molecular sieve / CH₂Cl₂ / -20 °C

12: 85 percent / n-Bu₄NF, silica gel / tetrahydrofuran

13: NaIO₄ / tetrahydrofuran; H₂O

14: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol

15: 94 percent / toluene

16: 18 percent / LDA / tetrahydrofuran / -78 °C

17: NaH / tetrahydrofuran

18: n-Bu₃SnH, AIBN / toluene / 110 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; silica gel; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(99)00413-X

Reference yield:

: 125877-98-7
(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>ethanol

: 228724-96-7
(S)-4-((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: Et₃N, DMAP / CH₂Cl₂

2: n-Bu₄NF / tetrahydrofuran

3: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 deg C to RT

4: L-selectride / tetrahydrofuran / -78 °C

5: imidazole, DMAP / dimethylformamide / 50 °C

6: PPTS / methanol

7: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂ / 0 °C

8: CH₂Cl₂

9: DIBAL / CH₂Cl₂ / -78 °C

10: 80 percent / t-BuOOH, Ti(O-i-Pr)4, (+)-diethyl tartrate, 4 A molecular sieve / CH₂Cl₂ / -20 °C

11: 85 percent / n-Bu₄NF, silica gel / tetrahydrofuran

12: NaIO₄ / tetrahydrofuran; H₂O

13: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol

14: 94 percent / toluene

15: 18 percent / LDA / tetrahydrofuran / -78 °C

16: NaH / tetrahydrofuran

17: n-Bu₃SnH, AIBN / toluene / 110 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; silica gel; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(99)00413-X