Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester

Base Information

• Chemical Name: Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester
• CAS No.: 374687-97-5
• Molecular Formula: C₃₃H₃₉NO₅
• Molecular Weight: 529.676

Synonyms:Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester

Chemical Property of Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester

There total 16 articles about Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl 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:

D-(-)-quinic acid (77-95-2) → Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester (374687-97-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 94 percent / conc. H₃PO₄ / 12 h / 180 °C

2.1: 98 percent Turnov_. / NaOMe / 2.5 h / 0 °C

3.1: 86 percent / 3 Angstroem molecular sieves; pyridinium dichromate / CH₂Cl₂; acetic acid / 24 h / 20 °C

4.1: 99 percent / POCl₃; pyridine / 0 - 20 °C

5.1: 93 percent / DIBALH / toluene / 1 h / -40 - 0 °C

6.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

6.2: 98 percent / nBu₄NI / tetrahydrofuran / 12 h / Heating

7.1: 92 percent / NMO; OsO₄ / acetone; H₂O / 48 h / 20 °C

8.1: NaH / tetrahydrofuran / 1 h / 0 °C

8.2: 98 percent / nBu₄NI / tetrahydrofuran / 3 h / 20 °C

9.1: pyridine; DMAP / 24 h

10.1: 100 percent / TFA; H₂O / CH₂Cl₂ / 24 h / 20 °C

11.1: toluene / 4 h / Heating

12.1: 1.48 g / P(OMe)3 / 24 h / Heating

13.1: 81 percent / NaIO₄; RuCl₃*3H₂O / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

14.1: 92 percent / K₂CO₃ / methanol / 3 h / 20 °C

15.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

16.1: 90 percent / Martin esulfurane dehydrating agent / benzene / 1 h / Heating

17.1: PPh₃; Pd(PPh₃)4 / acetonitrile / 0.5 h / 20 °C

17.2: 74 mg / acetonitrile / Heating

With pyridine; dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methyl-2-indolinone; Martins sulfurane; phosphoric acid; 3 A molecular sieve; water; sodium methylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; phosphorous acid trimethyl ester; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/jo010202t

Reference yield:

methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate (374687-81-7) → Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester (374687-97-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 93 percent / DIBALH / toluene / 1 h / -40 - 0 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 98 percent / nBu₄NI / tetrahydrofuran / 12 h / Heating

3.1: 92 percent / NMO; OsO₄ / acetone; H₂O / 48 h / 20 °C

4.1: NaH / tetrahydrofuran / 1 h / 0 °C

4.2: 98 percent / nBu₄NI / tetrahydrofuran / 3 h / 20 °C

5.1: pyridine; DMAP / 24 h

6.1: 100 percent / TFA; H₂O / CH₂Cl₂ / 24 h / 20 °C

7.1: toluene / 4 h / Heating

8.1: 1.48 g / P(OMe)3 / 24 h / Heating

9.1: 81 percent / NaIO₄; RuCl₃*3H₂O / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

10.1: 92 percent / K₂CO₃ / methanol / 3 h / 20 °C

11.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

12.1: 90 percent / Martin esulfurane dehydrating agent / benzene / 1 h / Heating

13.1: PPh₃; Pd(PPh₃)4 / acetonitrile / 0.5 h / 20 °C

13.2: 74 mg / acetonitrile / Heating

With pyridine; dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methyl-2-indolinone; Martins sulfurane; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/jo010202t

Reference yield:

(1R,2S,3S)-1,2-O-ethylpropylidene-5-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (374687-82-8) → Acetic acid (1S,2S,5R,6S)-5,6-bis-benzyloxy-4-benzyloxymethyl-2-propylamino-cyclohex-3-enyl ester (374687-97-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 98 percent / nBu₄NI / tetrahydrofuran / 12 h / Heating

2.1: 92 percent / NMO; OsO₄ / acetone; H₂O / 48 h / 20 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 98 percent / nBu₄NI / tetrahydrofuran / 3 h / 20 °C

4.1: pyridine; DMAP / 24 h

5.1: 100 percent / TFA; H₂O / CH₂Cl₂ / 24 h / 20 °C

6.1: toluene / 4 h / Heating

7.1: 1.48 g / P(OMe)3 / 24 h / Heating

8.1: 81 percent / NaIO₄; RuCl₃*3H₂O / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

9.1: 92 percent / K₂CO₃ / methanol / 3 h / 20 °C

10.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

11.1: 90 percent / Martin esulfurane dehydrating agent / benzene / 1 h / Heating

12.1: PPh₃; Pd(PPh₃)4 / acetonitrile / 0.5 h / 20 °C

12.2: 74 mg / acetonitrile / Heating

With pyridine; dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methyl-2-indolinone; Martins sulfurane; water; sodium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/jo010202t

upstream raw materials:

D-(-)-quinic acid

methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate

(1R,2S,3S)-1,2-O-ethylpropylidene-5-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

3,4-O-ethylpropylidenequinic acid-1,5-lactone

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