Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Base Information

Chemical Name:Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester
CAS No.:180592-85-2
Molecular Formula:C₄₀H₅₄O₇
Molecular Weight:646.865
Hs Code.:

Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Synonyms:Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

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Chemical Property of Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

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Technology Process of Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

There total 20 articles about Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl 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: 89.0%

: 100-52-7
benzaldehyde

: 157427-43-5
(3S,5R,6S,7R,8S)-8,9-Bis-benzyloxy-6-hydroxy-1-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-3,5,7-trimethyl-nonan-4-one

: 180592-85-2
Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -10 ℃; for 1h;

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4
1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

: 180592-85-2
Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 81 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

2: 100 percent / MeONa / methanol / 24 h / 25 °C

3: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 4 h, 2.) DMF, 40 deg C, 16 h

4: 1.) imidazole, NaH

5: 60 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 110 °C

6: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 20 min, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT, 7 h

7: 83 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 2 h / 40 °C

8: 1.) LDA / 1.) Et₂O, hexane, 0 deg C, 4 h, 2.) Et₂O, hexane, from -110 deg C to RT, 12 h

9: 97 percent / O₃ / CH₂Cl₂ / -78 °C

10: 1.) TiCl₄, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 2.5 h

11: 89 percent / SmI₂ / tetrahydrofuran / 1 h / -10 °C

With 1H-imidazole; sodium tetrahydroborate; samarium diiodide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; iodine; tri-n-butyl-tin hydride; sodium methylate; titanium tetrachloride; sodium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

Reference yield:

: 73-34-7
L-rhamnose

: 180592-85-2
Benzoic acid (1R,2S,3S,4S)-1-((1R,2S)-2,3-bis-benzyloxy-1-methyl-propyl)-3-hydroxy-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 91 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 81 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

3: 100 percent / MeONa / methanol / 24 h / 25 °C

4: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 4 h, 2.) DMF, 40 deg C, 16 h

5: 1.) imidazole, NaH

6: 60 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 110 °C

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 20 min, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT, 7 h

8: 83 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 2 h / 40 °C

9: 1.) LDA / 1.) Et₂O, hexane, 0 deg C, 4 h, 2.) Et₂O, hexane, from -110 deg C to RT, 12 h

10: 97 percent / O₃ / CH₂Cl₂ / -78 °C

11: 1.) TiCl₄, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 2.5 h

12: 89 percent / SmI₂ / tetrahydrofuran / 1 h / -10 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; samarium diiodide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; iodine; tri-n-butyl-tin hydride; sodium methylate; titanium tetrachloride; sodium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;