((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Base Information

Chemical Name:((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester
CAS No.:105281-32-1
Molecular Formula:C₂₁H₂₇NO₅
Molecular Weight:373.449
Hs Code.:

Synonyms:((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

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Chemical Property of ((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Chemical Property:

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Technology Process of ((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

There total 8 articles about ((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester 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:

: 105309-44-2
[(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

: 105281-32-1
((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Guidance literature:: With hydrogenchloride; oxalic acid; In tetrahydrofuran; water; at 60 ℃; for 8h; Yield given;
DOI:10.1021/jo00375a057

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 105281-32-1
((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 2 h

2: 85 percent / DIBAL / toluene / 0.5 h

3: 1.) NaH / 1.) Et₂O, RT, 15 min, 2.) Et₂O, from -15 deg C to RT, 30 min

4: xylene / 48 h / Heating

5: 82 percent / 1 N aq. KOH / tetrahydrofuran / 4 h / 60 °C

6: 1.3 g / H₂ / 10percent Pd/C / ethanol / 18 h / 2280 - 3040 Torr

7: 100 percent / Et₃N / tetrahydrofuran / 0 °C

8: oxalic acid, 12 N HCl / tetrahydrofuran; H₂O / 8 h / 60 °C

With hydrogenchloride; potassium hydroxide; hydrogen; oxalic acid; sodium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; toluene; xylene;
DOI:10.1021/jo00375a057

Reference yield:

: 90661-39-5
(E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 105281-32-1
((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / DIBAL / toluene / 0.5 h

2: 1.) NaH / 1.) Et₂O, RT, 15 min, 2.) Et₂O, from -15 deg C to RT, 30 min

3: xylene / 48 h / Heating

4: 82 percent / 1 N aq. KOH / tetrahydrofuran / 4 h / 60 °C

5: 1.3 g / H₂ / 10percent Pd/C / ethanol / 18 h / 2280 - 3040 Torr

6: 100 percent / Et₃N / tetrahydrofuran / 0 °C

7: oxalic acid, 12 N HCl / tetrahydrofuran; H₂O / 8 h / 60 °C

With hydrogenchloride; potassium hydroxide; hydrogen; oxalic acid; sodium hydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; toluene; xylene;
DOI:10.1021/jo00375a057