methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside

Base Information

• Chemical Name: methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside
• CAS No.: 138866-64-5
• Molecular Formula: C₂₉H₃₄O₅SSi
• Molecular Weight: 522.737

Synonyms:methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside

Chemical Property of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside

Chemical Property:

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Technology Process of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside

There total 1 articles about methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside 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: 82.0%

(2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran (130144-85-3) + phenylcarbonochloridothioate (1005-56-7) → methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside (138866-64-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 5 ℃;

DOI:10.1002/ardp.2503241203

Reference yield: 25.0%

methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside (138866-64-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranoside (138866-67-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 1h;

DOI:10.1002/ardp.2503241203

Reference yield: 24.0%

methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside (138866-64-5) + acrylonitrile (107-13-1,25014-41-9) → methyl 5-O-tert-butyldiphenylsilyl-3-(2-cyanoethyl)-2,3-dideoxy-α-D-erythro-pentofuranoside (138866-66-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 6h;

DOI:10.1002/ardp.2503241203

upstream raw materials:

(2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran

phenylcarbonochloridothioate

Downstream raw materials:

methyl 5-O-tert-butyldiphenylsilyl-3-(2-cyanoethyl)-2,3-dideoxy-α-D-erythro-pentofuranoside

methyl 5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranoside

1-(5-O-tert-butyl-diphenylsilyl-3-(2-cyanoethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)uracil

1-(5-O-tert-butyldiphenylsilyl-3-(2-cyanoethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)uracil

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