(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol

Base Information

• Chemical Name: (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol
• CAS No.: 160531-41-9
• Molecular Formula: C₂₁H₃₆O₄
• Molecular Weight: 352.514
• Mol file: 160531-41-9.mol

Synonyms:(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol

Chemical Property of (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol

There total 18 articles about (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol 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%

(2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid methyl ester (160531-20-4) → (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol (160531-41-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

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

Reference yield:

(S)-4-methyl-pentane-1,3-diol (16451-50-6) → (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol (160531-41-9)

Guidance literature:

Multi-step reaction with 12 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

8: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

9: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

10: 93 percent / tetrahydrofuran / 10 h / 70 °C

11: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

12: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

With hydrogenchloride; dmap; lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; 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-methylpentanal (160531-15-7) → (2S,4R,5R,7S)-7-Benzyloxy-5-methoxymethoxy-2,4,8-trimethyl-nonan-1-ol (160531-41-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 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

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

3: 96 percent / i-Pr₂NEt / 2 h / Ambient temperature

4: 91 percent / 1.0 M DIBAL / tetrahydrofuran; hexane / 0.17 h / -78 °C

5: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 deg C, 30 min; 0 deg C, 1 h; -78 deg C, 30 min; 0 deg C, 1 h

6: 1.) 30percent aq. H₂O₂, LiOH*H₂O / 1.) H₂O, THF, 0 deg C, 1.5 h, 2.) CHCl₃, Et₂O

7: 93 percent / tetrahydrofuran / 10 h / 70 °C

8: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

9: 97 percent / 1.0 M LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

With lithium hydroxide; lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;

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

upstream raw materials:

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

4-methylpent-2-en-1-ol

ethyl 4-methylpent-2-enoate

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

Downstream raw materials:

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

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

(2S,4S,6R,7S,9S)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid

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