(2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester
CAS No.:228724-97-8
Molecular Formula:C₂₄H₃₃NO₈
Molecular Weight:463.528
Hs Code.:

(2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

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Chemical Property of (2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

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Technology Process of (2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

There total 19 articles about (2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl 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:

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

: 228724-97-8
(2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 20 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

18: FeCl₃, SiO₂ / CHCl₃

19: Jones reagent / acetone

20: benzene; methanol

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; jones reagent; 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; iron(III) chloride; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
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

: 228724-97-8
(2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 21 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

19: FeCl₃, SiO₂ / CHCl₃

20: Jones reagent / acetone

21: benzene; methanol

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; 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; iron(III) chloride; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(99)00413-X

Reference yield:

: (2R,3aR,7aR)-Hexahydro-furo[3,2-b]pyran-2-carbaldehyde

: 228724-97-8
(2R,3aR,7aR)-2-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

2: 94 percent / toluene

3: 18 percent / LDA / tetrahydrofuran / -78 °C

4: NaH / tetrahydrofuran

5: n-Bu₃SnH, AIBN / toluene / 110 °C

6: FeCl₃, SiO₂ / CHCl₃

7: Jones reagent / acetone

8: benzene; methanol

With sodium chlorite; sodium dihydrogenphosphate; jones reagent; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; silica gel; iron(III) chloride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; chloroform; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(99)00413-X