(1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one

Base Information

• Chemical Name: (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one
• CAS No.: 334968-92-2
• Molecular Formula: C₄₃H₇₀O₇Si₂
• Molecular Weight: 755.196
• Mol file: 334968-92-2.mol

Synonyms:(1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one

Chemical Property of (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one

There total 17 articles about (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one 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: 88.0%

(S)-1-Benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-propan-2-one (334968-75-1) + (2S,3R)-7-Benzyloxy-2-methyl-3-triethylsilanyloxy-heptanal (334968-76-2) → (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one (334968-92-2)

Guidance literature:

With dicyclohexylboron chloride; triethylamine; In pentane;

DOI:10.1021/ol015652m

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one (334968-92-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine

2: LiBH₄ / methanol; diethyl ether

3: 80 percent / Dess-Martin periodinane

4: 88 percent / Cy₂BCl; Et₃N / pentane

With 2,6-dimethylpyridine; lithium borohydride; dicyclohexylboron chloride; Dess-Martin periodane; triethylamine; In methanol; diethyl ether; pentane; 3: Dess-Martin oxidation;

DOI:10.1021/ol015652m

Reference yield:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hex-5-enal (334968-80-8) → (1S,4S,5R,6R)-1,10-Bis-benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-4-hydroxy-5-methyl-6-triethylsilanyloxy-decan-2-one (334968-92-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 74 percent / Bu₂BOTf; DIPEA / CH₂Cl₂ / -78 °C

2: LiBH₄ / methanol; diethyl ether

3: Et₃N; DMAP

4: OsO₄; NaIO₄

5: POCl₃; pyridine / 70 °C

6: i-Bu₂AlH

7: Dess-Martin periodinane

8: diethyl ether

9: Dess-Martin periodinane

10: 88 percent / Cy₂BCl; Et₃N / pentane

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; dicyclohexylboron chloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In methanol; diethyl ether; dichloromethane; pentane; 7: Dess-Martin oxidation / 9: Dess-Martin oxidation;

DOI:10.1021/ol015652m

upstream raw materials:

(S)-1-Benzyloxy-1-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-propan-2-one

(2S,3R)-7-Benzyloxy-2-methyl-3-triethylsilanyloxy-heptanal

triethylsilyl trifluoromethyl sulfonate

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hex-5-enal

Downstream raw materials:

(2R,4S,5R,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-benzyloxy-[(2R,3S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-3,4-dihydro-2H-pyran-2-yl]-methyl}-2-methoxy-5-methyl-tetrahydro-pyran-4-ol