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

Base Information

• Chemical Name: (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol
• CAS No.: 143376-16-3
• Molecular Formula: C₃₁H₅₀O₈Si
• Molecular Weight: 578.819
• Mol file: 143376-16-3.mol

Synonyms:(2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol

Chemical Property of (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol

There total 12 articles about (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol 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:

1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-L-lyxo-hex-1-enitol (129985-34-8) → (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol (143376-16-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1.5h;

DOI:10.1021/ja00180a037

Reference yield:

benzyl bromide (100-39-0) → (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol (143376-16-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) 60percent NaH in oil / 1.) THF, 30 min, 2.) RT, 14 h

2: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) 0 deg C, 30 min, 2.) 0 deg C, 30 min

3: 57 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

4: 75 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

5: 80 percent / imidazole / CH₂Cl₂ / 29 h / Heating

6: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) -78 deg C, 30 min, 2.) -78 deg C, 30 min

7: 93 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

8: lithium aluminum hydride / diethyl ether / 1.5 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; triphenylstannane; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja00180a037

Reference yield:

1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol (129985-30-4) → (2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol (143376-16-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) 60percent NaH in oil / 1.) THF, 30 min, 2.) RT, 14 h

2: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) 0 deg C, 30 min, 2.) 0 deg C, 30 min

3: 57 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

4: 75 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

5: 80 percent / imidazole / CH₂Cl₂ / 29 h / Heating

6: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) -78 deg C, 30 min, 2.) -78 deg C, 30 min

7: 93 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

8: lithium aluminum hydride / diethyl ether / 1.5 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; triphenylstannane; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/ja00180a037

upstream raw materials:

1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-L-lyxo-hex-1-enitol

benzyl bromide

1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol

(2S,3R)-3-benzyloxy-2-methyl-3,4-dihydro-2H-pyran

Downstream raw materials:

1,5-anhydro-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-α-L-lyxo-hexopyranosyl>-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol