(2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

Base Information

• Chemical Name: (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol
• CAS No.: 1606140-50-4
• Molecular Formula: C₂₀H₂₅NO₃
• Molecular Weight: 327.423
• Mol file: 1606140-50-4.mol

Synonyms:(2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

Chemical Property of (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

There total 4 articles about (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol 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:

methanol (67-56-1) + (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol (1606140-55-9) → (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol (1606140-50-4) + (2R,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

Guidance literature:

(2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol; With hydrogenchloride; In diethyl ether; at 20 ℃; for 0.0833333h;

With ozone; In methanol; dichloromethane; at -78 ℃;

methanol; Overall yield = 91 %; Overall yield = 493 mg; diastereoselective reaction; Further stages;

DOI:10.1016/j.tet.2014.03.055

Reference yield:

C25H31NO3 (1613225-09-4) → (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol (1606140-50-4) + (2R,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / methanol / -20 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / diethyl ether / 0.08 h / 20 °C

3.2: -78 °C

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/j.tet.2014.03.055

Reference yield:

(4E,2R,3R,αR)-tert-butyl 2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)hex-4-enoate (487042-22-8) → (2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol (1606140-50-4) + (2R,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / -20 - 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

4.1: hydrogenchloride / diethyl ether / 0.08 h / 20 °C

4.2: -78 °C

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;

DOI:10.1016/j.tet.2014.03.055

upstream raw materials:

methanol

(2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol

C₂₅H₃₁NO₃

(4E,2R,3R,αR)-tert-butyl 2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)hex-4-enoate