(S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Base Information

• Chemical Name: (S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol
• CAS No.: 161147-32-6
• Molecular Formula: C₃₃H₄₀O₆Si
• Molecular Weight: 560.763
• Mol file: 161147-32-6.mol

Synonyms:(S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Chemical Property of (S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

There total 1 articles about (S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-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:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) + trimethylsilylacetylene (1066-54-2) → (R)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (161147-33-7) + (S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (161147-32-6)

Guidance literature:

With n-butyllithium; magnesium bromide; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, Et₂O, -5 deg C, 30 min, 2.) -30 deg C to r.t.;

DOI:10.1021/jo00108a030

Reference yield: 96.0%

(S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (161147-32-6) → methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside (103597-22-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1021/jo00108a030

Reference yield:

(S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (161147-32-6) → Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-D-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester (161147-42-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / Bu₄NF / tetrahydrofuran / 0.25 h / Ambient temperature

2: 75 percent / Ph₃P, Zn(N₃)2*2py, diisopropyl azodicarboxylate / toluene / 0.5 h / Ambient temperature

3: 1,3-propanedithiol, Et₃N / methanol / 24 h / 45 °C

4: pyridine / 3 h / Ambient temperature

5: OsO₄, aq. NaIO₄ / tetrahydrofuran / 5 h / 45 °C

6: CH₂Cl₂

With pyridine; 1.3-propanedithiol; sodium periodate; osmium(VIII) oxide; zinc azide * 2 pyridine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo00108a030

upstream raw materials:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

trimethylsilylacetylene

Downstream raw materials:

methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside

methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside

Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside

(S)-1-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-ynylamine