3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose

Base Information

• Chemical Name: 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose
• CAS No.: 157555-90-3
• Molecular Formula: C₂₀H₃₂O₄SSi
• Molecular Weight: 396.623

Synonyms:3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose

Chemical Property of 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose

Chemical Property:

Purity/Quality:

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Technology Process of 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose

There total 3 articles about 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose 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: 61.0%

3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-O-(p-tolylsulfonyl)-α-D-xylofuranose (92413-83-7) + thiophenol (108-98-5) → 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose (157555-90-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 50 ℃; for 16h;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose (157555-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DBU / CH₂Cl₂ / 17 h / Ambient temperature

2: 61 percent / DBU / benzene / 16 h / 50 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; benzene;

Reference yield:

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose (6893-65-8,20513-95-5,20513-96-6,34981-06-1,40429-51-4,110349-61-6) → 3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose (157555-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DBU / CH₂Cl₂ / 17 h / Ambient temperature

2: 61 percent / DBU / benzene / 16 h / 50 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; benzene;

upstream raw materials:

3-(O-tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-O-(p-tolylsulfonyl)-α-D-xylofuranose

thiophenol

tert-butyldimethylsilyl chloride

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose

Downstream raw materials:

6,10-anhydro-3-O-(tert-butyldimethylsilyl)-8,9-dideoxy-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-glycero-L-ido-decofuranos-7-ulose

(S)-2-{[(3aR,5S,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-phenylsulfanyl-methyl}-dihydro-pyran-3-one

3-(O-tert-butyldimethylsilyl)-5-chloro-1,2-O-isopropylidene-5-S-phenyl-5-thio-α-D-xylofuranose

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