1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol
• CAS No.: 142270-10-8
• Molecular Formula: C₃₄H₃₄O₅
• Molecular Weight: 522.641

Synonyms:1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol

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Technology Process of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol

There total 12 articles about 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol 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%

4-methoxyphenylboronic acid (5720-07-0) + 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol (64978-35-4) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol (142270-10-8)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 12h; chemoselective reaction; Sealed tube;

DOI:10.1021/jacs.9b02312 DOI:10.1021/jacs.9b02312

Reference yield: 55.0%

1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene (221184-12-9) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol (142270-10-8)

Guidance literature:

With Mo(CHCMe2Ph)2; In toluene; at 60 ℃;

DOI:10.1021/jo982331o

Reference yield: 33.0%

1-bromo-4-methoxy-benzene (104-92-7) + 3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal (105938-01-0) → (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran (130912-27-5) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-(4-methoxyphenyl)-D-arabino-hex-1-enitol (142270-10-8)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 3h; Heating;

DOI:10.1016/S0008-6215(00)90552-4

upstream raw materials:

1-bromo-4-methoxy-benzene

3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal

1-[1-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enyloxy)-vinyl]-4-methoxy-benzene

3,4,6-tri-O-benzyl-β-D-arabinofuranoside

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