methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

Base Information

Chemical Name:methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate
CAS No.:288848-44-2
Molecular Formula:C₂₃H₃₁NO₆
Molecular Weight:417.502
Hs Code.:

Synonyms:methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

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Chemical Property of methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

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Technology Process of methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

There total 5 articles about methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate 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: 62.0%

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

: 288848-38-4
(1'R,3'R)-2-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]acetaldehyde

: 288848-44-2
methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

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

: 288848-44-2
methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 85 percent / LiBH₄ / tetrahydrofuran / Heating

3: 95 percent / PDC / CH₂Cl₂ / 4 h / 20 °C

4: 62 percent / t-BuOK / CH₂Cl₂ / 54 h / 20 °C

With dipyridinium dichromate; lithium borohydride; potassium tert-butylate; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; benzene; 1: Condensation / 2: Reduction / 3: Oxidation / 4: 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

: 288848-44-2
methyl (1'R,3'R)-2-benzyloxycarbonylamino-4-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-butenoate

Guidance literature:: Multi-step reaction with 5 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: 95 percent / PDC / CH₂Cl₂ / 4 h / 20 °C

5: 62 percent / t-BuOK / CH₂Cl₂ / 54 h / 20 °C

With potassium hydroxide; dipyridinium dichromate; lithium borohydride; potassium tert-butylate; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene; 1: Methylation / 2: Condensation / 3: Reduction / 4: Oxidation / 5: Condensation;
DOI:10.1021/jo991773c