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

Base Information

Chemical Name:(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid
CAS No.:1025824-33-2
Molecular Formula:C₂₄H₄₀O₆
Molecular Weight:424.578
Hs Code.:

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

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

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

There total 18 articles about (2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid 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:

: 160531-42-0
(S)-3-((2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoyl)-4-isopropyl-oxazolidin-2-one

: 1025824-33-2
(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1021/jo00096a003

Reference yield:

: 16451-50-6
(S)-4-methyl-pentane-1,3-diol

: 1025824-33-2
(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid

Guidance literature:: Multi-step reaction with 17 steps

1: Et₃N, DMAP / CH₂Cl₂ / 13 h / 20 °C

2: NaH / dimethylformamide / 2.5 h / Ambient temperature

3: conc. HCl / methanol; tetrahydrofuran / 4 h / 30 °C

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

5: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

6: Me₃Al / tetrahydrofuran / 2 h / -19 - -6 °C

7: i-Pr₂NEt / 2 h

8: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

9: Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

10: aq. LiOH, H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

11: diethyl ether; CHCl₃ / 0.08 h / Ambient temperature

12: 93 percent / tetrahydrofuran / 10 h / Heating

13: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

14: LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

15: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) -78 deg C to 0 deg C, 10 min

16: Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

17: aq. LiOH, H₂O₂ / tetrahydrofuran / 1.5 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; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00096a003

Reference yield:

: 100-39-0
benzyl bromide

: 1025824-33-2
(2S,3R,4S,6R,7R,9S)-9-Benzyloxy-3-hydroxy-7-methoxymethoxy-2,4,6,10-tetramethyl-undecanoic acid

Guidance literature:: Multi-step reaction with 16 steps

1: NaH / dimethylformamide / 2.5 h / Ambient temperature

2: conc. HCl / methanol; tetrahydrofuran / 4 h / 30 °C

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

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

5: Me₃Al / tetrahydrofuran / 2 h / -19 - -6 °C

6: i-Pr₂NEt / 2 h

7: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

8: Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

9: aq. LiOH, H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

10: diethyl ether; CHCl₃ / 0.08 h / Ambient temperature

11: 93 percent / tetrahydrofuran / 10 h / Heating

12: 79 percent / Bu₃SnH / toluene / 0.22 h / Heating

13: LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

14: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) -78 deg C to 0 deg C, 10 min

15: Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

16: aq. LiOH, H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

With hydrogenchloride; 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; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00096a003