Benzyl 23-O-benzyloxymethylisolasalocid A

Base Information

• Chemical Name: Benzyl 23-O-benzyloxymethylisolasalocid A
• CAS No.: 152934-55-9
• Molecular Formula: C₄₉H₆₈O₉
• Molecular Weight: 801.074
• Mol file: 152934-55-9.mol

Synonyms:Benzyl 23-O-benzyloxymethylisolasalocid A

Chemical Property of Benzyl 23-O-benzyloxymethylisolasalocid A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 23-O-benzyloxymethylisolasalocid A

There total 28 articles about Benzyl 23-O-benzyloxymethylisolasalocid A 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:

(2S,5R)-2-<(1R)-1-Benzyloxymethoxyethyl>-2-ethyl-5-formyltetrahydrofuran (128531-41-9) → Benzyl 23-O-benzyloxymethylisolasalocid A (152934-55-9)

Guidance literature:

Multi-step reaction with 16 steps

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

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

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

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

5: 100 percent / LiAlH₄ / tetrahydrofuran / 0 °C

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

7: 98 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

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

9: 95 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature

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

11: 99 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Ambient temperature

12: 94 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 1.2 h / Ambient temperature

13: 1) Mg / 1) THF, 2) THF, 30 min, -20 deg C

14: 100 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

15: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

With 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; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; benzene;

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

Reference yield:

(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,3-dioxan-4-yl>propyl phenyl sulfone (131967-58-3) → Benzyl 23-O-benzyloxymethylisolasalocid A (152934-55-9)

Guidance literature:

Multi-step reaction with 16 steps

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

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

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

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

5: 100 percent / LiAlH₄ / tetrahydrofuran / 0 °C

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

7: 98 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

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

9: 95 percent / Pb(OAc)4 / benzene / 0.17 h / Ambient temperature

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

11: 99 percent / n-Bu₄NF / tetrahydrofuran / 12 h / Ambient temperature

12: 94 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 1.2 h / Ambient temperature

13: 1) Mg / 1) THF, 2) THF, 30 min, -20 deg C

14: 100 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

15: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

With 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; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; benzene;

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

Reference yield:

(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) → Benzyl 23-O-benzyloxymethylisolasalocid A (152934-55-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Mg / 1) THF, 2) THF, 30 min, -20 deg C

2: 100 percent / pyridinium chlorochromate, 3A molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

3: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

With 3 A molecular sieve; hydrogen; magnesium; pyridinium chlorochromate; palladium on activated charcoal; In dichloromethane; ethyl acetate;

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

upstream raw materials:

3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

(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

(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

Downstream raw materials:

Isolasalocid 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.