Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester
• CAS No.: 871483-58-8
• Molecular Formula: C₂₀H₂₉NO₄
• Molecular Weight: 347.455

Synonyms:Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

There total 2 articles about Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester 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: 80.0%

isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (137100-81-3) + benzyl-methyl-amine (103-67-3) → Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester (871483-58-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Heating;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

D-glucal triacetate (2873-29-2) → Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester (871483-58-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / BiCl₃ / acetonitrile

2: 80 percent / Pd(PPh₃)4 / tetrahydrofuran / Heating

With bismuth(III) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; acetonitrile; 1: Ferrier glycosidation;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield: 98.0%

Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester (871483-58-8) → [(2S,3S,6S)-3-(Benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-yl]-methanol (871483-80-6)

Guidance literature:

With methanol; potassium carbonate;

DOI:10.1016/j.bmcl.2005.08.062

upstream raw materials:

isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

benzyl-methyl-amine

D-glucal triacetate

Downstream raw materials:

[(2S,3S,6S)-3-(Benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-yl]-methanol

benzyl-[2-(tert-butyl-dimethyl-silanyloxymethyl)-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl]-methyl-amine

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-(2-{[(2S,3S,6S)-6-isobutoxy-2-(3-phenyl-propionyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-methyl-amino}-acetylamino)-succinamic acid benzyl ester

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