acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside

Base Information

• Chemical Name: acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside
• CAS No.: 154367-73-4
• Molecular Formula: C₂₂H₃₄O₆SeSi
• Molecular Weight: 501.554

Synonyms:acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside

Chemical Property of acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside

Chemical Property:

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Technology Process of acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside

There total 5 articles about acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside 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: 78.0%

Acetic acid (2R,3S,4S,5R,6R)-6-chloro-2-methyl-5-phenylselanyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yl ester → acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside (154367-73-4) + acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-α-D-fuco-pyranoside

Guidance literature:

In tetrahydrofuran; for 5h;

DOI:10.1021/ja00113a013

Reference yield:

triethylsilyl chloride (994-30-9) → acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside (154367-73-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / dimethylformamide

2: Et₃N, DMAP / CH₂Cl₂

3: 1) CH₂Cl₂, 0 deg C, 2) THF

With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)91806-9

Reference yield:

6-deoxy-D-glucal (134355-03-6) → acetyl 4-O-acetyl-2-deoxy-2-selenophenyl-3-O-(triethyl)silyl-β-D-fuco-pyranoside (154367-73-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / dimethylformamide

2: Et₃N, DMAP / CH₂Cl₂

3: 1) CH₂Cl₂, 0 deg C, 2) THF

With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)91806-9

upstream raw materials:

Phenylselenyl chloride

silver(I) acetate

4-O-acetyl-3-O-((triethyl)silyl)-D-fucal

triethylsilyl chloride

Downstream raw materials:

acetyl 4-O-acetyl-2-deoxy-2-(selenophenyl)-β-D-fuco-pyranoside

2-naphthyl 4-O-acetyl-3-O<3-O-((tert-butyldimethyl)silyl)-2,6-dideoxy-2-iodo-4-O-methyl-α-D-talo-pyranosyl>-2,6-dideoxy-2-(selenophenyl)-β-D-galacto-pyranoside

4-O-acetyl-3-O<3-O-((tert-butyldimethyl)silyl)-2,6-dideoxy-2-iodo-4-O-methyl-α-D-talo-pyranosyl>-2,6-dideoxy-2-(selenophenyl)-α-D-galacto-pyranose

Acetic acid (2R,3R,4S,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-((2R,3R,4S,5S,6R)-2,5-diacetoxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-4-yloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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