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

Base Information

• Chemical Name: (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal
• CAS No.: 152934-49-1
• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.612
• Mol file: 152934-49-1.mol

Synonyms:(2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal

Chemical Property of (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal

There total 25 articles about (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal 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: 94.0%

(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) → (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal (152934-49-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)98022-5

Reference yield:

(2R,3R,4S)-4-benzyloxymethyl-3-formyloxy-2-methylhexanal (110653-58-2) → (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal (152934-49-1)

Guidance literature:

Multi-step reaction with 20 steps

1: 99 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 deg C to r.t.

2: 98 percent / pyridine / Ambient temperature

3: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 6 h / Ambient temperature

4: 98 percent / d-camphorsulfonic acid / benzene / 0.5 h / Ambient temperature

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 deg C to r.t.

6: 96 percent / pyridine / 2 h / Ambient temperature

7: 94 percent / NaI / acetone / 8 h / Heating

8: 93 percent / dimethylformamide / 6 h / 60 °C

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

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

11: 84 percent / Al-Hg / tetrahydrofuran; H₂O / 3 h / Ambient temperature

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

13: 100 percent / LiAlH₄ / tetrahydrofuran / 0 °C

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

15: 98 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

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

17: 95 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature

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

19: 99 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Ambient temperature

20: 94 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 1.2 h / Ambient temperature

With pyridine; 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium dithionite; oxalyl dichloride; aluminium amalgam; 3 A molecular sieve; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 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

Reference yield:

(2S,3S,4S)-4-Benzyloxymethyl-2-methylhexane-1,3-diol (152934-35-5) → (2R)-2-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethenyl-3-methyltetrahydrofur-2-yl>butanal (152934-49-1)

Guidance literature:

Multi-step reaction with 19 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

19: 94 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 1.2 h / Ambient temperature

With pyridine; 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium dithionite; oxalyl dichloride; aluminium amalgam; 3 A molecular sieve; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 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:

(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

(2S,5R)-2-<(1R)-1-Benzyloxymethoxyethyl>-2-ethyl-5-formyltetrahydrofuran

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

(3S)-1-<(2R,5S)-<(1R)-1-Benzyloxymethoxyethyl>-5-ethyltetrahydrofur-2-yl>-3-<(4S,5S)-5-ethyl-2,2-dimethyl-1,3-dioxan-4-yl>butan-1-one

Downstream raw materials:

(4S)-4-<(2S,3S,5R)-5-<(2R,5S)-5-((1R)-1-Benzyloxymethoxyethyl)-5-ethyltetrahydrofur-2-yl>-5-ethyl-3-methyltetrahydrofur-2-yl>hexan-3-one

Isolasalocid A

Benzyl 23-O-benzyloxymethylisolasalocid A

lasalocid (X 537 A)

Refernces

• 1、 Noda,Horita,Oikawa,Yonemitsu. "Stereoselective synthesis of polyether antibiotics, lasalocid A and isolasalocid A, via a chelation-controlled formation of tetrahydrofuran rings under thermodynamic conditions". . p. 6035 - 6038. Retrieved 2007/10/02.