(R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one

Base Information

• Chemical Name: (R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one
• CAS No.: 1329450-98-7
• Molecular Formula: C₁₇H₂₃NO₄S
• Molecular Weight: 337.44

Synonyms:(R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one

Chemical Property of (R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one

Chemical Property:

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Technology Process of (R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one

There total 3 articles about (R_S,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one 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%

2-tert-butyldimethylsilyloxyfuran (121896-38-6) + (R)-N-[(1E)-2-(benzyloxy)ethylidene]-2-methylpropane-2-sulfinamide (393536-17-9) → (RS,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one (1329450-98-7) + C17H23NO4S

Guidance literature:

With water; samarium(III) trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 16h; Reagent/catalyst; Overall yield = 93 %; diastereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201201618

Reference yield:

2-tert-butyldimethylsilyloxyfuran (121896-38-6) + (R)-N-[(1E)-2-(benzyloxy)ethylidene]-2-methylpropane-2-sulfinamide (393536-17-9) → (S,S)-5-[(R)-(benzyloxymethyl)(tert-butanesulfinylamino)methyl]furan-2(5H)-on (1329451-00-4) + (RS,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one (1329450-98-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol2020384

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (RS,5R)-5-[(1S)-(benzyloxymethyl)(tert-butylsulfinylamino)methyl]furan-2(5H)-one (1329450-98-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate; magnesium sulfate / dichloromethane / 20 h / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; magnesium sulfate; In dichloromethane; 2: Mannich reaction;

DOI:10.1021/ol2020384

upstream raw materials:

benzyloxyacetoaldehyde

2-tert-butyldimethylsilyloxyfuran

(R)-N-[(1E)-2-(benzyloxy)ethylidene]-2-methylpropane-2-sulfinamide

Downstream raw materials:

(-)-deoxoprosophylline

(R,S)-5-[(R)-(benzyloxymethyl)(tert-butanesulfinylamino)methyl]furan-2(4H)-one

(5R,6S)-6-(benzyloxymethyl)-5-(tert-butyldimethylsilyloxy)piperidin-2-one

(5R,6S)-6-(benzyloxymethyl)-5-hydroxypiperidin-2-one

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