(1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester
CAS No.:290838-45-8
Molecular Formula:C₂₇H₃₆N₂O₆
Molecular Weight:484.593
Hs Code.:

Synonyms:(1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

There total 7 articles about (1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl 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:

: 290838-43-6
(1S,2R,5R)-methyl 2-benzyloxycarbonylamino-5-hydroxycyclohex-3-enecarboxylate

: 290838-45-8
(1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

1.2: Bu₄NN₃ / CH₂Cl₂ / 1.5 h / 0 °C

1.3: P(n-Bu)3 / CH₂Cl₂; H₂O / 10 h / 20 °C

2.1: CH₂Cl₂; H₂O / 24 h

3.1: H₂ / 10percent Pd/C / methanol / 2068.65 Torr

4.1: DIEA; DMAP / CH₂Cl₂ / 27 h

5.1: 60 percent / NaOMe / methanol / 5 h / Heating

6.1: TFA / 0.5 h

7.1: DIEA; DMAP / CH₂Cl₂ / 24 h

With dmap; hydrogen; sodium methylate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In methanol; dichloromethane; water; 1.1: mesylation / 1.2: Substitution / 1.3: Reduction / 2.1: Acylation / 3.1: Catalytic hydrogenation / 4.1: Acylation / 5.1: Isomerization / 6.1: Boc-deprotection / 7.1: Acylation;
DOI:10.1021/jo000277h

Reference yield:

: (1S,2R,5S)-5-Amino-2-benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid methyl ester

: 290838-45-8
(1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: CH₂Cl₂; H₂O / 24 h

2: H₂ / 10percent Pd/C / methanol / 2068.65 Torr

3: DIEA; DMAP / CH₂Cl₂ / 27 h

4: 60 percent / NaOMe / methanol / 5 h / Heating

5: TFA / 0.5 h

6: DIEA; DMAP / CH₂Cl₂ / 24 h

With dmap; hydrogen; sodium methylate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In methanol; dichloromethane; water; 1: Acylation / 2: Catalytic hydrogenation / 3: Acylation / 4: Isomerization / 5: Boc-deprotection / 6: Acylation;
DOI:10.1021/jo000277h

Reference yield:

: 267230-30-8
(1S,2R,5S)-methyl 2-benzyloxycarbonylamino-5-t-butoxycarbonylaminocyclohex-3-enecarboxylate

: 290838-45-8
(1R,2R,5R)-5-(Adamantan-1-yloxycarbonylamino)-2-benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / 10percent Pd/C / methanol / 2068.65 Torr

2: DIEA; DMAP / CH₂Cl₂ / 27 h

3: 60 percent / NaOMe / methanol / 5 h / Heating

4: TFA / 0.5 h

5: DIEA; DMAP / CH₂Cl₂ / 24 h

With dmap; hydrogen; sodium methylate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In methanol; dichloromethane; 1: Catalytic hydrogenation / 2: Acylation / 3: Isomerization / 4: Boc-deprotection / 5: Acylation;
DOI:10.1021/jo000277h