((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

Base Information

• Chemical Name: ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate
• CAS No.: 1421054-16-1
• Molecular Formula: C₂₇H₂₉NO₆S
• Molecular Weight: 495.596

Synonyms:((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

Chemical Property of ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

Chemical Property:

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Technology Process of ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

There total 3 articles about ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate 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: 58.0%

4-methoxy-benzaldehyde (123-11-5) + benzonitrile (100-47-0) + (R)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate (501365-06-6) → ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate (1421054-16-1)

Guidance literature:

With boron trifluoride diethyl etherate; at 0 - 25 ℃; stereoselective reaction;

DOI:10.1021/ol303364j

Reference yield:

(R)-pent-4-ene-1,2-diol (238758-59-3) → ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate (1421054-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 0.83 h / 25 °C

2: boron trifluoride diethyl etherate / 0 - 25 °C

With boron trifluoride diethyl etherate; di(n-butyl)tin oxide; triethylamine; In dichloromethane; 2: |Ritter Amidation;

DOI:10.1021/ol303364j

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → ((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate (1421054-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 0.83 h / 25 °C

2: boron trifluoride diethyl etherate / 0 - 25 °C

With boron trifluoride diethyl etherate; di(n-butyl)tin oxide; triethylamine; In dichloromethane; 2: |Ritter Amidation;

DOI:10.1021/ol303364j

upstream raw materials:

4-methoxy-benzaldehyde

benzonitrile

(R)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

(R)-pent-4-ene-1,2-diol

Downstream raw materials:

((2R,4S,6S)-4-(benzamido)-tetrahydro-6-(4-methoxyphenyl)-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

N-((1S,3R)-1-hydroxy-1-(4-methoxyphenyl)hex-5-en-3-yl)benzamide

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