(2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol

Base Information

• Chemical Name: (2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol
• CAS No.: 152934-35-5
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• Mol file: 152934-35-5.mol

Synonyms:(2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol

Chemical Property of (2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol

There total 1 articles about (2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol 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: 99.0%

(2R,3R,4S)-4-benzyloxymethyl-3-formyloxy-2-methylhexanal (110653-58-2) → (2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol (152934-35-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 0.0833333h; 0 deg C to r.t.;

DOI:10.1016/S0040-4020(01)87185-4

Reference yield:

(2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol (152934-35-5) → (2S)-2-<(2S,3S,5R)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butan-1-ol (131967-61-8)

Guidance literature:

Multi-step reaction with 18 steps

1: 98 percent / pyridine / Ambient temperature

2: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 6 h / Ambient temperature

3: 98 percent / d-camphorsulfonic acid / benzene / 0.5 h / Ambient temperature

4: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 deg C to r.t.

5: 96 percent / pyridine / 2 h / Ambient temperature

6: 94 percent / NaI / acetone / 8 h / Heating

7: 93 percent / dimethylformamide / 6 h / 60 °C

8: 1) n-BuLi / 1) hexane, Et₂O, r.t., 2) THF, hexane, -75 deg C

9: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 3 h

10: 77 percent / Al-Hg / tetrahydrofuran; H₂O / 3 h / Ambient temperature

11: 1) n-BuLi / 1) Et₂O, hexane, -78 deg C, 30 min, 2) Et₂O, 2 h

12: 97 percent / LiAlH₄ / tetrahydrofuran / 0 °C

13: ZnBr₂ / CH₂Cl₂ / 78 h / Ambient temperature; various amounts of ZnBr₂; also with d-camphorsulfonic acid, variation of condition

14: 100 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

15: 1) OsO₄, N-methylmorpholine N-oxide, 2) Na₂S₂O₄, Celite / 1) acetone, H₂O, 6 h, r.t., 2) acetone, H₂O, overnight, r.t.

16: 98 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature

17: 1) n-BuLi / 1) hexane, THF, 1 h, 0 deg C, 2) THF, 15 h, r.t.

18: 100 percent / n-Bu₄NF / tetrahydrofuran / 7 h / Ambient temperature

With pyridine; 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium dithionite; oxalyl dichloride; aluminium amalgam; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; zinc dibromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)87185-4

Reference yield:

(2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol (152934-35-5) → (2S)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butan-1-ol (131967-62-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 98 percent / pyridine / Ambient temperature

2: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 6 h / Ambient temperature

3: 98 percent / d-camphorsulfonic acid / benzene / 0.5 h / Ambient temperature

4: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 deg C to r.t.

5: 96 percent / pyridine / 2 h / Ambient temperature

6: 94 percent / NaI / acetone / 8 h / Heating

7: 93 percent / dimethylformamide / 6 h / 60 °C

8: 1) n-BuLi / 1) Et₂O, hexane, 15 min, r.t., 2) Et₂O, hexane, -75 deg C, 2 h

9: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h, 2) 3 h

10: 84 percent / Al-Hg / tetrahydrofuran; H₂O / 3 h / Ambient temperature

11: 1) n-BuLi / 1) Et₂O, hexane, -78 deg C, 30 min, 2) Et₂O, 2 h

12: 100 percent / LiAlH₄ / tetrahydrofuran / 0 °C

13: d-camphorsulfonic acid / benzene / Ambient temperature; 1) 30 sec, sonication, 2) 3 h

14: 98 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

15: 1) OsO₄, N-methylmorpholine oxide, 2) Na₂S₂O₄, Celite / 1) acetone, H₂O, 6 h, r.t., 2) H₂O, acetone, overnight, r.t.

16: 95 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature

17: 1) n-BuLi / 1) hexane, THF, 0 deg C, 1 h, 2) THF, r.t., overnight

18: 99 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Ambient temperature

With pyridine; 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium dithionite; oxalyl dichloride; aluminium amalgam; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)87185-4

upstream raw materials:

(2R,3R,4S)-4-benzyloxymethyl-3-formyloxy-2-methylhexanal

Downstream raw materials:

(2S,3S,4S)-4-Benzyloxymethyl-3-hydroxy-2-methyl-1-pivaloyloxyhexane

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,3-dioxan-4-yl>propyl phenyl sulfone

(2S)-2-<(2S,3S,5R)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butan-1-ol

(2S)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butan-1-ol

Refernces