methyl N-benzenesulfonyl-N,O⁷-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside

Base Information

• Chemical Name: methyl N-benzenesulfonyl-N,O⁷-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside
• CAS No.: 157793-78-7
• Molecular Formula: C₁₈H₂₅NO₆S
• Molecular Weight: 383.466

Synonyms:methyl N-benzenesulfonyl-N,O⁷-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside

Chemical Property of methyl N-benzenesulfonyl-N,O⁷-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside

Chemical Property:

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Technology Process of methyl N-benzenesulfonyl-N,O⁷-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside

There total 3 articles about methyl N-benzenesulfonyl-N,O⁷-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside 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: 65.0%

methyl 6-(N-benzenesulfonylamino)-N,O-isopropylidene-2,3,6,8-tetradeoxy-α-D-erythrooct-2-enopyranos-4-uloside (142037-59-0) → methyl N-benzenesulfonyl-N,O7-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside (157793-78-7)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; for 0.5h;

Reference yield:

(1R,2R,3R)-N-benzenesulfonyl-N,O3-isopropylidene-1-(2-furyl)-2-aminobutane-1,3-diol (141990-12-7) → methyl N-benzenesulfonyl-N,O7-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside (157793-78-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / sodium hydrogen carbonate, m-chloroperbenzoic acid / CH₂Cl₂

2: 80 percent / Ag₂O / diethyl ether / 24 h / 25 °C

3: 3 percent / 1.6 M diisobutylaluminum hydride / tetrahydrofuran / 0.5 h / -70 °C

With diisobutylaluminium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In tetrahydrofuran; diethyl ether; dichloromethane;

Reference yield:

6-amino-N-benzenesulfonyl-N,O-isopropylidene-2,3,6,8-tetradeoxy-α-D-ribo-oct-2-enopyranos-4-ulose (142037-63-6) → methyl N-benzenesulfonyl-N,O7-isopropylidene-6-amino-2,3,6,8-tetradeoxy-α-D-altro-oct-2-enopyranoside (157793-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Ag₂O / diethyl ether / 24 h / 25 °C

2: 3 percent / 1.6 M diisobutylaluminum hydride / tetrahydrofuran / 0.5 h / -70 °C

With diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; diethyl ether;

upstream raw materials:

methyl 6-(N-benzenesulfonylamino)-N,O-isopropylidene-2,3,6,8-tetradeoxy-α-D-erythrooct-2-enopyranos-4-uloside

(1R,2R,3R)-N-benzenesulfonyl-N,O³-isopropylidene-1-(2-furyl)-2-aminobutane-1,3-diol

6-amino-N-benzenesulfonyl-N,O-isopropylidene-2,3,6,8-tetradeoxy-α-D-ribo-oct-2-enopyranos-4-ulose

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