(2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal

Base Information

• Chemical Name: (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal
• CAS No.: 142945-16-2
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.498
• Mol file: 142945-16-2.mol

Synonyms:(2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal

Chemical Property of (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal

There total 13 articles about (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal 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: 89.0%

(2S,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonan-1-ol (952677-55-3) → (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal (142945-16-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4039(00)79858-3

Reference yield:

(E)-5-(benzyloxy)pent-2-en-1-ol (89923-31-9) → (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal (142945-16-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 72 percent / (-)-DET, Ti(OⁱPr)4, ^tBuOOH

2: 60 percent / CuI

3: 84 percent

4: 84 percent / NaH

5: 100 percent / H₂ / Pd(OH)2-C

6: 94 percent / (COCl)2, DMSO, Et₃N

7: 58 percent / Bu₂BOTf, Et₃N

8: 75 percent / ⁱPr₂NEt

9: 83 percent / lithium methoxyborohydride

10: 98 percent / ⁱPr₂NEt

11: 83 percent / LiMeOBH₃ / Heating

12: 100 percent / Bu₄NF

13: 89 percent / (COCl)2, DMSO, Et₃N

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trihydrido-(methanolato-O)-borate^(1-); lithium salt; sodium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; copper(l) iodide; palladium hydroxide - carbon;

DOI:10.1016/S0040-4039(00)79858-3

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → (2R,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonanal (142945-16-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 60 percent / CuI

2: 84 percent

3: 84 percent / NaH

4: 100 percent / H₂ / Pd(OH)2-C

5: 94 percent / (COCl)2, DMSO, Et₃N

6: 58 percent / Bu₂BOTf, Et₃N

7: 75 percent / ⁱPr₂NEt

8: 83 percent / lithium methoxyborohydride

9: 98 percent / ⁱPr₂NEt

10: 83 percent / LiMeOBH₃ / Heating

11: 100 percent / Bu₄NF

12: 89 percent / (COCl)2, DMSO, Et₃N

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trihydrido-(methanolato-O)-borate^(1-); lithium salt; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; copper(l) iodide; palladium hydroxide - carbon;

DOI:10.1016/S0040-4039(00)79858-3

upstream raw materials:

(2S,3R,5R,6S)-9-Benzyloxy-3-methoxy-5-methoxymethoxy-2,6-dimethyl-nonan-1-ol

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

(E)-5-(benzyloxy)pent-2-en-1-ol

5-Benzyloxy-2-methylpentane-1,3-diol

Downstream raw materials:

(E)-(4R,5R,9S,10R,12R,13S)-16-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4,10-dimethoxy-12-methoxymethoxy-5,9,13-trimethyl-hexadec-7-en-6-one