(2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether
• CAS No.: 152934-54-8
• Molecular Formula: C₃₁H₅₂O₅Si
• Molecular Weight: 532.836

Synonyms:(2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether

Chemical Property of (2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether

There total 18 articles about (2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether 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: 98.0%

1-{(2R,4S,5S)-2-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-4-methyl-tetrahydro-furan-2-yl}-2-(4-methoxy-phenyl)-ethane-1,2-diol → (2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether (152934-54-8)

Guidance literature:

With lead(IV) acetate; In benzene; Ambient temperature;

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

Reference yield:

(2R,3R,4S)-4-benzyloxymethyl-3-formyloxy-2-methylhexanal (110653-58-2) → (2S)-2-<(2S,3S,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether (152934-54-8)

Guidance literature:

Multi-step reaction with 17 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) hexane, Et₂O, r.t., 2) THF, hexane, -75 deg C

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

11: 77 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: 97 percent / LiAlH₄ / tetrahydrofuran / 0 °C

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

15: 100 percent / imidazole / CH₂Cl₂ / 3 h / Ambient temperature

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

17: 98 percent / Pb(OAc)4 / benzene / 0.17 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; 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,5S)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-formyl-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether (152934-54-8)

Guidance literature:

Multi-step reaction with 16 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

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; 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

upstream raw materials:

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

(3S)-1-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3-<(4S,5S)-5-ethyl-2,2-dimethyl-1,3-dioxan-4-yl>butan-1-one

(2S)-2-<(2S,3S,5R)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>-3-methyltetrahydrofur-2-yl>butyl tert-butyldimethylsilyl ether

(2S)-2-<(2S,3S,5R)-5-<(2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>-3-methyltetrahydrofur-2-yl>butan-1-ol

Downstream raw materials:

(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

lasalocid (X 537 A)

lasalocid benzyl ester

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