methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside

Base Information

• Chemical Name: methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside
• CAS No.: 494211-85-7
• Molecular Formula: C₁₈H₂₄O₄S
• Molecular Weight: 336.452

Synonyms:methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside

Chemical Property of methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside

Chemical Property:

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Technology Process of methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside

There total 2 articles about methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside 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:

(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole (29325-28-8,828937-31-1) → methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside (494211-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 4 h / 0 - 23 °C

2: 204 mg / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

With sodium hydroxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; benzene; 2: Suzuki cross-coupling;

DOI:10.1021/jo026163i

Reference yield:

phenyl α-bromovinyl sulfide (80485-53-6) + (3aR,4R,6R,6aR)-4-[2-(9-Bora-bicyclo[3.3.1]non-9-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole → methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside (494211-85-7)

Guidance literature:

With sodium hydroxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; benzene; for 4h; Heating;

DOI:10.1021/jo026163i

Reference yield:

methyl 5,6,8-trideoxy-2,3-O-(1-methylethylidene)-7-S-phenyl-7-thio-β-D-ribo-oct-7-enofuranoside (494211-85-7) → (3aR,4R,6R,6aR)-4-Methoxy-2,2-dimethyl-6-((E)-3-phenylsulfanyl-but-2-enyl)-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:

With boron trifluoride diethyl etherate; In various solvent(s); at 23 ℃; for 48h;

DOI:10.1021/jo026163i

upstream raw materials:

phenyl α-bromovinyl sulfide

(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole

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