1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

Base Information

• Chemical Name: 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone
• CAS No.: 682807-88-1
• Molecular Formula: C₃₉H₄₆O₆Si
• Molecular Weight: 638.876

Synonyms:1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

Chemical Property of 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

There total 3 articles about 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone 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: 85.0%

[(Z)-1-Methoxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane (682807-87-0) → 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone (682807-88-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1055/s-2004-815403

Reference yield:

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose (113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9) → 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone (682807-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄; EtOH

2: 2,6-lutidine / CH₂Cl₂ / 0 °C

3: tetrahydrofuran / -78 °C

4: I₂; aq. CaCO₃ / tetrahydrofuran

With 2,6-dimethylpyridine; sodium tetrahydroborate; ethanol; iodine; calcium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2004-815403

Reference yield:

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (89064-71-1) → 1-Trimethylsilanyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone (682807-88-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: tetrahydrofuran / -78 °C

3: I₂; aq. CaCO₃ / tetrahydrofuran

With 2,6-dimethylpyridine; iodine; calcium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2004-815403

upstream raw materials:

[(Z)-1-Methoxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

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