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

Base Information

• Chemical Name: (1S,4S,5R,6R)-1,10-Bis-benzyloxy-4-hydroxy-5-methyl-1-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-6-triethylsilanyloxy-decan-2-one
• CAS No.: 438625-80-0
• Molecular Formula: C₄₃H₇₀O₇Si₂
• Molecular Weight: 755.196
• Mol file: 438625-80-0.mol

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

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

There total 1 articles about (1S,4S,5R,6R)-1,10-Bis-benzyloxy-4-hydroxy-5-methyl-1-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-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: 93.0%

(2S,3R)-7-Benzyloxy-2-methyl-3-triethylsilanyloxy-heptanal (334968-76-2) + (S)-1-Benzyloxy-1-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-propan-2-one → (1S,4S,5R,6R)-1,10-Bis-benzyloxy-4-hydroxy-5-methyl-1-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-6-triethylsilanyloxy-decan-2-one (438625-80-0)

Guidance literature:

With dicyclohexylboron chloride; triethylamine; In pentane;

DOI:10.1021/ja0262683

Reference yield: 72.0%

methanol (67-56-1) + (1S,4S,5R,6R)-1,10-Bis-benzyloxy-4-hydroxy-5-methyl-1-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-6-triethylsilanyloxy-decan-2-one (438625-80-0) → (2R,3R,4S)-2-{(S)-Benzyloxy-[(2R,4S,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-methyl}-3-methyl-3,4-dihydro-2H-pyran-4-ol (438625-81-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1021/ja0262683

Reference yield:

(1S,4S,5R,6R)-1,10-Bis-benzyloxy-4-hydroxy-5-methyl-1-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-6-triethylsilanyloxy-decan-2-one (438625-80-0) → [4-[(2R,3S,4S,6R)-4-(tert-butyldimethylsiloxy)-6-[(S)-[(2R,3S,4S)-3,4-dihydro-3-methyl-4-(triethylsiloxy)-2H-pyran-2-yl]-(triethylsiloxy)methyl]tetrahydro-6-methoxy-3-methyl-2H-pyran-2-yl]butyl]triphenylphosphonium iodide

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / PPTS / CH₂Cl₂

2: imidazole / CH₂Cl₂

3: KN(SiMe₃)2 / tetrahydrofuran / -78 °C

4: LDBB / tetrahydrofuran

5: Et₃N; DMAP

6: imidazole / CH₂Cl₂

7: NaI / acetone

8: Li₂CO₃ / acetonitrile; benzene

With 1H-imidazole; dmap; lithium 4,4′-di(tert-butyl)biphenyl; pyridinium p-toluenesulfonate; lithium carbonate; potassium hexamethylsilazane; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1021/ja0262683

upstream raw materials:

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

Downstream raw materials:

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

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

Toluene-4-sulfonic acid 4-{(2R,3S,4S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-3-methyl-6-[(S)-((2R,3S,4S)-3-methyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-2-yl)-triethylsilanyloxy-methyl]-tetrahydro-pyran-2-yl}-butyl ester