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

Base Information

• Chemical Name: (R)-4-[((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 228725-00-6
• Molecular Formula: C₂₆H₃₇NO₈
• Molecular Weight: 491.582
• Mol file: 228725-00-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (R)-4-[((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-hydroxy-methyl]-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: 18.0%

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + (2R,3aR,7aR)-Hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester (228724-88-7) → (R)-4-[((2S,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (228724-95-6) + (R)-4-[((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (228725-00-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(99)00413-X

Reference yield:

tert-Butyl-dimethyl-((2R,3S)-2-vinyl-tetrahydro-pyran-3-yloxy)-silane (125877-97-6) → (R)-4-[((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (228725-00-6)

Guidance literature:

Multi-step reaction with 16 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: 75 percent / LDA / tetrahydrofuran / -78 °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; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; silica gel; L-Selectride; 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:

(2R,3aR,7aR)-Hexahydro-furo[3,2-b]pyran-2-carbaldehyde → (R)-4-[((2R,3aR,7aR)-2-Benzyloxycarbonyl-hexahydro-furo[3,2-b]pyran-2-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (228725-00-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 94 percent / toluene

3: 75 percent / LDA / tetrahydrofuran / -78 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; lithium diisopropyl amide; In tetrahydrofuran; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00413-X

upstream raw materials:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(2R,3aR,7aR)-Hexahydro-furo[3,2-b]pyran-2-carboxylic acid benzyl ester

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

(2R,3aR,7aR)-Hexahydro-furo[3,2-b]pyran-2-carboxylic acid

Downstream raw materials:

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

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