(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran
• CAS No.: 130912-27-5
• Molecular Formula: C₃₃H₃₂O₄
• Molecular Weight: 492.615

Synonyms:(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran

Chemical Property of (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran

Chemical Property:

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Technology Process of (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran

There total 33 articles about (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran 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: 94.0%

1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol (64978-35-4) + phenylboronic acid (98-80-6) → (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran (130912-27-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 13h; Solvent; Reagent/catalyst; Temperature; chemoselective reaction; Catalytic behavior; Mechanism; Sealed tube;

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

Reference yield: 90.0%

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol (64978-35-4) → (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyl-3,4-dihydro-2H-pyran (130912-27-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tricyclohexylphosphine tetrafluoroborate; potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 13h; chemoselective reaction; Sealed tube;

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

Reference yield: 88.0%

bromobenzene (108-86-1,52753-63-6) + 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)

Guidance literature:

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

DOI:10.1039/c39900001191

upstream raw materials:

bromobenzene

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

1-bromo-4-methoxy-benzene

tetra-O-benzyl glucopyranosyl chloride

Downstream raw materials:

3,4,6-tri-O-benzyl-1-C-phenyl-α-D-glucopyranose

(2R,3S,4R,6R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyltetrahydro-2H-pyran

(4,6-di-O-benzyl-2,3-dideoxy-β-D-erythro-hexopyranosyl)benzene

(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-ol

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