2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

Base Information

Chemical Name:2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose
CAS No.:136174-78-2
Molecular Formula:C₃₇H₄₄O₈S₂Si
Molecular Weight:708.969
Hs Code.:

Synonyms:2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

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Chemical Property of 2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

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Technology Process of 2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

There total 4 articles about 2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose 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: 81.0%

: 136174-76-0
4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-α-D-gluco-pyranose

: 135-19-3
β-naphthol

: 136174-78-2
2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

: 136174-96-4
2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-α-D-gluco-pyranose

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 ℃; Yields of byproduct given;
DOI:10.1021/jo00020a003

Reference yield: 6.0%

: 136174-76-0,136174-77-1,136174-94-2,136174-95-3
4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-D-gluco-pyranose

: 135-19-3
β-naphthol

: 136174-78-2
2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

: 136174-96-4
2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-α-D-gluco-pyranose

Guidance literature:: With 4 A molecular sieve; triphenylphosphine; diethylazodicarboxylate; In toluene; for 1.5h;
DOI:10.1021/ja00113a013

Reference yield:

: 129693-97-6
4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal

: 136174-78-2
2-naphthyl 4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-(thiophenyl)-6-O-tosyl-β-D-gluco-pyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 2) Ag₂CO₃ / 1) CCl₄, -20 deg C 2) THF, H₂O

2: 81 percent / Ph₃P, diethyl azodicarboxylate / toluene / 0 °C

With triphenylphosphine; silver carbonate; diethylazodicarboxylate; In toluene;
DOI:10.1021/jo00020a003