(3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone

Base Information

• Chemical Name: (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone
• CAS No.: 171897-02-2
• Molecular Formula: C₃₁H₃₉NO₄Si
• Molecular Weight: 517.74

Synonyms:(3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone

Chemical Property of (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone

Chemical Property:

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Technology Process of (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone

There total 3 articles about (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone 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:

acetone (67-64-1) + (4S,5S)-4-benzylamino-5-((t-butyldiphenylsilyl)oxymethyl)dihydro-2-(3H)furanone (171896-93-8) → (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone (171897-02-2)

Guidance literature:

With ammonium chloride; lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min;

DOI:10.1016/0040-4039(95)01417-G

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone (171897-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) imidazole / 1.) MeOH, 0 deg C, 36 h, 2.) DMF, RT, 2 d

2: 1.) lithiumhexamethyldisilazide / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 1.5 h

With 1H-imidazole; lithium hexamethyldisilazane;

DOI:10.1016/0957-4166(96)00255-8

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (3R,4S,5S)-4-benzylamino-5-(t-butyldiphenylsilyl)oxymethyl-3-((1-hydroxy-1-methyl)-1-ethyl)dihydro-2(3H)furanone (171897-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) imidazole / 1.) MeOH, 0 deg C, 36 h, 2.) DMF, RT, 2 d

2: 1.) lithiumhexamethyldisilazide / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 1.5 h

With 1H-imidazole; lithium hexamethyldisilazane;

DOI:10.1016/0957-4166(96)00255-8

upstream raw materials:

acetone

(4S,5S)-4-benzylamino-5-((t-butyldiphenylsilyl)oxymethyl)dihydro-2-(3H)furanone

(5S)-5-(hydroxymethyl)-5H-furan-2-one

tert-butylchlorodiphenylsilane

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