methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

Base Information

Chemical Name:methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate
CAS No.:288848-43-1
Molecular Formula:C₂₇H₃₃NO₅
Molecular Weight:451.563
Hs Code.:

Synonyms:methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

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Chemical Property of methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

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Technology Process of methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

There total 10 articles about methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate 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: 52.0%

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: 288848-37-3
(1R,3R)-3-(2'-benzyloxyethyl)-2,2-dimethylcyclobutanocarbaldehyde

: 288848-43-1
methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

Guidance literature:: With potassium tert-butylate; In dichloromethane; at 20 ℃; for 54h;
DOI:10.1021/jo991773c

Reference yield:

: 52305-35-8
methyl 2-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]acetate

: 288848-43-1
methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / pyridinium p-toluenesulfonate / benzene / 4 h / Heating

2: 85 percent / LiBH₄ / tetrahydrofuran / Heating

3: 90 percent / NaH / dimethylformamide / 72 h / 20 °C

4: 98 percent / pyridinium p-toluenesulfonate / acetone / 8 h / Heating

5: 41 percent / aq. NaOBr / dioxane / 0 - 20 °C

6: 92 percent / KOH / diethyl ether; ethanol / 1 h / 20 °C

7: 68 percent / LiBH₄ / tetrahydrofuran / Heating

8: 91 percent / PDC / CH₂Cl₂ / 4 h / 20 °C

9: 52 percent / t-BuOK / CH₂Cl₂ / 54 h / 20 °C

With potassium hydroxide; dipyridinium dichromate; lithium borohydride; sodium hypobromide; potassium tert-butylate; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 1: Condensation / 2: Reduction / 3: Alkylation / 4: Hydrolysis / 5: Oxidation / 6: Methylation / 7: Reduction / 8: Oxidation / 9: Condensation;
DOI:10.1021/jo991773c

Reference yield:

: 473-72-3,17879-35-5,61376-92-9,61826-55-9,64396-97-0,127062-09-3,52305-34-7
(1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid

: 288848-43-1
methyl (1'S,3'R)-2-benzyloxycarbonylamino-3-[3'-(2-benzyloxyethyl)-2',2'-dimethylcyclobutyl]-(Z)-2-propenoate

Guidance literature:: Multi-step reaction with 10 steps

1: KOH / diethyl ether; ethanol / 1 h / 20 °C

2: 81 percent / pyridinium p-toluenesulfonate / benzene / 4 h / Heating

3: 85 percent / LiBH₄ / tetrahydrofuran / Heating

4: 90 percent / NaH / dimethylformamide / 72 h / 20 °C

5: 98 percent / pyridinium p-toluenesulfonate / acetone / 8 h / Heating

6: 41 percent / aq. NaOBr / dioxane / 0 - 20 °C

7: 92 percent / KOH / diethyl ether; ethanol / 1 h / 20 °C

8: 68 percent / LiBH₄ / tetrahydrofuran / Heating

9: 91 percent / PDC / CH₂Cl₂ / 4 h / 20 °C

10: 52 percent / t-BuOK / CH₂Cl₂ / 54 h / 20 °C

With potassium hydroxide; dipyridinium dichromate; lithium borohydride; sodium hypobromide; potassium tert-butylate; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 1: Methylation / 2: Condensation / 3: Reduction / 4: Alkylation / 5: Hydrolysis / 6: Oxidation / 7: Methylation / 8: Reduction / 9: Oxidation / 10: Condensation;
DOI:10.1021/jo991773c