5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone

Base Information

• Chemical Name: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone
• CAS No.: 140193-76-6
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358

Synonyms:5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone

Chemical Property of 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone

Chemical Property:

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Technology Process of 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone

There total 11 articles about 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone 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: 83.0%

(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine (100777-91-1) + 2-tert-butyldimethylsilyloxyfuran (121896-38-6) → 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone (140193-76-6)

Guidance literature:

With t-butyldimethylsiyl triflate; In dichloromethane; at -80 ℃; for 3h;

DOI:10.1016/S0957-4166(99)00051-8

Reference yield: 83.0%

(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine (100777-91-1) + 2-tert-butyldimethylsilyloxyfuran (121896-38-6) → (R)-5-[(R)-Benzylamino-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5H-furan-2-one + 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone (140193-76-6)

Guidance literature:

With t-butyldimethylsiyl triflate; In dichloromethane; at -80 ℃; for 3h;

DOI:10.1016/S0957-4166(97)00344-3

Reference yield: 66.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine (131319-74-9) → 5-[Benzylamino-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5H-furan-2-one (140193-75-5,140193-76-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -85 ℃; for 6h;

DOI:10.1016/S0040-4020(01)88132-1

upstream raw materials:

(furan-2-yloxy)-trimethylsilane

(R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine

benzylamine

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(1'S,4''S,5S)-5-[benzylamino-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-4,5-dihydrofuran-2(3H)-one

(4'S,5S,6S)-1-benzyl-6-(2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxypiperidin-2-one

(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

(4'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-yl)piperidin-2-one

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