(+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide

Base Information

• Chemical Name: (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide
• CAS No.: 643727-58-6
• Molecular Formula: C₂₉H₅₅NO₅Si₂
• Molecular Weight: 553.93
• Mol file: 643727-58-6.mol

Synonyms:(+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide

Chemical Property of (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide

There total 13 articles about (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide 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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (+)-(2S,3R,4S,5R)-6-benzyloxy-5-(tert-butyldimethylsiloxy)-3-hydroxy-2,4-dimethyl-N-methoxy-N-methylhexanamide (642993-72-4) → (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide (643727-58-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -40 ℃; for 3h;

DOI:10.1021/jo035068m

Reference yield:

1-(1H-benzotriazol-1-yl)-2-benzyloxyethan-1-one (642993-51-9) → (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide (643727-58-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

1.2: 72 percent / tetrahydrofuran / 1.75 h / -78 - 20 °C

2.1: (R,R)-ruthenium complex; Et₃N; HCO₂H / CH₂Cl₂ / 16 h / 20 °C

3.1: bis(trimethylsilylperoxide); rac. trans-N,N'-bis(p-toluenesulfonyl)cylohexan-1,2-diamine; SnCl₄ / molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 20 °C

3.2: acetic acid / tetrahydrofuran; H₂O / 18 h / 20 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

6.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

7.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

7.2: CH₂Cl₂ / 3 h / -78 - 0 °C

7.3: 80 percent / aq. H₂O₂ / aq. phosphate buffer; CH₂Cl₂; methanol / 1 h / 0 °C / pH 7

8.1: AlMe₃ / CH₂Cl₂; toluene / 0.5 h / -15 - 20 °C

8.2: 97 percent / CH₂Cl₂ / 24 h / -15 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -40 °C

With 2,6-dimethylpyridine; formic acid; oxalyl dichloride; bis-trimethylsilanyl peroxide; rac. trans-N,N'-bis(p-toluenesulfonyl)cylohexan-1,2-diamine; (R,R)-ruthenium; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tin(IV) chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; 4 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Baeyer-Villiger oxidation / 6.1: Swern reacrion;

DOI:10.1021/jo035068m

Reference yield:

4-benzyloxy-2-methyl-1-phenylbutane-1,3-dione (426833-01-4) → (+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethyl-N-methoxy-N-methylhexanamide (643727-58-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (R,R)-ruthenium complex; Et₃N; HCO₂H / CH₂Cl₂ / 16 h / 20 °C

2.1: bis(trimethylsilylperoxide); rac. trans-N,N'-bis(p-toluenesulfonyl)cylohexan-1,2-diamine; SnCl₄ / molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 20 °C

2.2: acetic acid / tetrahydrofuran; H₂O / 18 h / 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

4.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

6.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

6.2: CH₂Cl₂ / 3 h / -78 - 0 °C

6.3: 80 percent / aq. H₂O₂ / aq. phosphate buffer; CH₂Cl₂; methanol / 1 h / 0 °C / pH 7

7.1: AlMe₃ / CH₂Cl₂; toluene / 0.5 h / -15 - 20 °C

7.2: 97 percent / CH₂Cl₂ / 24 h / -15 °C

8.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -40 °C

With 2,6-dimethylpyridine; formic acid; oxalyl dichloride; bis-trimethylsilanyl peroxide; rac. trans-N,N'-bis(p-toluenesulfonyl)cylohexan-1,2-diamine; (R,R)-ruthenium; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tin(IV) chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 4 A molecular sieve; In hexane; dichloromethane; toluene; 2.1: Baeyer-Villiger oxidation / 5.1: Swern reacrion;

DOI:10.1021/jo035068m

upstream raw materials:

tert-butyldimethylsilyl chloride

(+)-(2S,3R,4S,5R)-6-benzyloxy-5-(tert-butyldimethylsiloxy)-3-hydroxy-2,4-dimethyl-N-methoxy-N-methylhexanamide

t-butyldimethylsiyl triflate

benzyloxyacetic acid

Downstream raw materials:

(+)-(2S,3R,4S,5R)-6-benzyloxy-3,5-bis(tert-butyldimethylsiloxy)-2,4-dimethylhexanal

2-[(1S,2R,3S,4R)-5-Benzyloxy-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-pentyl]-[1,3]dithiane