(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal

Base Information

• Chemical Name: (2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal
• CAS No.: 160531-17-9
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• Mol file: 160531-17-9.mol

Synonyms:(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal 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: 91.0%

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide (160531-39-5) → (2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal (160531-17-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(S)-4-methyl-pentane-1,3-diol (16451-50-6) → (2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal (160531-17-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

2: 1.) 60percent NaH, 2.) concd HCl / 1.) DMF, 0 deg C to room temp., 2.5 h, 2.) MeOH, THF, 30 deg C, 4 h

3: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

5: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

6: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

7: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

With hydrogenchloride; dmap; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81206-0

Reference yield:

(S)-3-Benzyloxy-4-methyl-pentan-1-ol (160531-37-3) → (2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanal (160531-17-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / (COCl)2, DMSO; Et₃N / CH₂Cl₂ / -78 deg C, 20 min; -78 to 0 deg C, 0 deg C, 15 min

2: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 50 min; -78 deg C, 30 min; 0 deg C, 1 h

3: 92 percent / Me₃Al / tetrahydrofuran; toluene / -19 deg C, 2 h; -6 deg C, 2 h;

4: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

5: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)81206-0

upstream raw materials:

(2S,3R,5S)-5-Benzyloxy-3-methoxymethoxy-2,6-dimethyl-heptanoic acid methoxy-methyl-amide

4-methylpent-2-en-1-ol

ethyl 4-methylpent-2-enoate

(S)-4-methyl-pentane-1,3-diol

Downstream raw materials:

(S)-3-((2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoyl)-4-isopropyl-oxazolidin-2-one

(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid

(3S,9S,11S,13R,14S,16S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-14-hydroxy-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione