((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

Base Information

Chemical Name:((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester
CAS No.:499195-45-8
Molecular Formula:C₃₀H₃₀N₂O₆
Molecular Weight:514.578
Hs Code.:

Synonyms:((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

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Chemical Property of ((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

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Technology Process of ((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

There total 8 articles about ((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-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: 33.0%

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 499195-41-4
((1S,3R,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxycarbonylamino-2-oxo-cyclohexyl)-carbamic acid benzyl ester

: 499195-45-8
((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

Guidance literature:: (methoxymethyl)triphenylphosphonium chloride; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.166667h;

((1S,3R,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxycarbonylamino-2-oxo-cyclohexyl)-carbamic acid benzyl ester; In tetrahydrofuran; at 0 - 23 ℃; for 3h;

With camphor-10-sulfonic acid; In dichloromethane; at 23 ℃; for 16h;
DOI:10.1016/S0960-894X(02)00759-X

Reference yield:

: 236115-61-0
[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate

: 499195-45-8
((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 94 percent / CSA / CH₂Cl₂ / 48 h / 23 °C

2.1: 95 percent / NaOMe / methanol / 4 h / 23 °C

3.1: 93 percent / NaH / dimethylformamide / 4 h / 0 - 23 °C

4.1: 85 percent / DDQ; water / CH₂Cl₂ / 3 h / 23 °C

5.1: PMe₃; NH₄OH; pyridine / tetrahydrofuran / 4 h / 23 °C

6.1: NaHCO₃ / dioxane; H₂O / 20 h / 23 °C

7.1: 93 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.58 h / -60 - 23 °C

8.1: LiHMDS / tetrahydrofuran / 0.17 h / 0 °C

8.2: tetrahydrofuran / 3 h / 0 - 23 °C

8.3: 33 percent / CSA / CH₂Cl₂ / 16 h / 23 °C

With pyridine; ammonium hydroxide; oxalyl dichloride; camphor-10-sulfonic acid; water; sodium methylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Staudinger reduction / 7.1: Swern oxidation / 8.2: Wittig reaction;
DOI:10.1016/S0960-894X(02)00759-X

Reference yield:

: 870180-36-2
(1S,2R,3R,4S,6R)-4,6-Diazido-3-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

: 499195-45-8
((1S,4R,5R)-4-Benzyloxy-5-benzyloxycarbonylamino-2-formyl-cyclohex-2-enyl)-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / NaH / dimethylformamide / 4 h / 0 - 23 °C

2.1: 85 percent / DDQ; water / CH₂Cl₂ / 3 h / 23 °C

3.1: PMe₃; NH₄OH; pyridine / tetrahydrofuran / 4 h / 23 °C

4.1: NaHCO₃ / dioxane; H₂O / 20 h / 23 °C

5.1: 93 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.58 h / -60 - 23 °C

6.1: LiHMDS / tetrahydrofuran / 0.17 h / 0 °C

6.2: tetrahydrofuran / 3 h / 0 - 23 °C

6.3: 33 percent / CSA / CH₂Cl₂ / 16 h / 23 °C

With pyridine; ammonium hydroxide; oxalyl dichloride; water; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Staudinger reduction / 5.1: Swern oxidation / 6.2: Wittig reaction;
DOI:10.1016/S0960-894X(02)00759-X