methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside

Base Information

• Chemical Name: methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside
• CAS No.: 1431846-00-2
• Molecular Formula: C₄₉H₅₄O₁₀
• Molecular Weight: 802.962

Synonyms:methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside

Chemical Property of methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside

There total 4 articles about methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside 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: 60.0%

methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside (1431845-99-6) → methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside (1431846-00-2)

Guidance literature:

methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201209697

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose (109010-30-2) → methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside (1431846-00-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

1.2: 3.5 h / 0 °C / Inert atmosphere

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-methyl-pyrrolidin-2-one / acetonitrile / 14.17 h / 100 °C / Inert atmosphere; Microwave irradiation

3.1: hydrogen / methanol; tetrahydrofuran / 5.5 h / 750.08 Torr / Inert atmosphere

4.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; borane-THF; hydrogen; In tetrahydrofuran; methanol; hexane; acetonitrile; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 2.1: |Stille Cross Coupling;

DOI:10.1002/anie.201209697

Reference yield:

(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside (1431845-83-8) → methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside (1431846-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-methyl-pyrrolidin-2-one / acetonitrile / 14.17 h / 100 °C / Inert atmosphere; Microwave irradiation

2.1: hydrogen / methanol; tetrahydrofuran / 5.5 h / 750.08 Torr / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.2: 2 h / 0 - 20 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane-THF; hydrogen; In tetrahydrofuran; methanol; acetonitrile; 1.1: |Stille Cross Coupling;

DOI:10.1002/anie.201209697

upstream raw materials:

methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside

(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose

(3E)-methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methylene-α-D-glucopyranoside

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