Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 205869-99-4
• Molecular Formula: C₅₁H₇₀O₂₆
• Molecular Weight: 1099.1
• Mol file: 205869-99-4.mol

Synonyms:Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

There total 13 articles about Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl 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:

1,2:5,6-diacetone-D-glucose (582-52-5) → Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (205869-99-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) NaH, tetrabutylammonium iodide / 1.) THF, 0 deg C -> room temperature, 2.) THF, 50 deg C, 2 h

2: 81 percent / Dowex 50 (H⁽¹⁺⁾) / H₂O / 2 h / 70 °C

3: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

4: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

5: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

7: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH₂Cl₂, 15 min, 2.) dioxane, water, 20 min

8: 89 percent / pyridine / 1 h

9: 96 percent / NaOMe / methanol; CH₂Cl₂ / 4.5 h

10: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, room temperature, 24 h

11: 53 percent / pyridine / 8 h / Ambient temperature

12: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature

13: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 30 min, 2.) CH₂Cl₂, room temperature, 45 min

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; ethanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Dowex 50 (H⁽¹⁺⁾); hydrogen bromide; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; mercury dibromide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water;

DOI:10.1016/S0008-6215(97)00249-8

Reference yield:

3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside (101475-83-6) → Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (205869-99-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 81 percent / Dowex 50 (H⁽¹⁺⁾) / H₂O / 2 h / 70 °C

2: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

3: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

4: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

6: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH₂Cl₂, 15 min, 2.) dioxane, water, 20 min

7: 89 percent / pyridine / 1 h

8: 96 percent / NaOMe / methanol; CH₂Cl₂ / 4.5 h

9: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, room temperature, 24 h

10: 53 percent / pyridine / 8 h / Ambient temperature

11: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature

12: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 30 min, 2.) CH₂Cl₂, room temperature, 45 min

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; ethanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Dowex 50 (H⁽¹⁺⁾); hydrogen bromide; hydrogen; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; mercury dibromide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water;

DOI:10.1016/S0008-6215(97)00249-8

Reference yield:

3-O-benzyl-D-glucopyranose (65877-63-6,97590-76-6,99396-09-5,5531-09-9) → Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (205869-99-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

2: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

3: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

5: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH₂Cl₂, 15 min, 2.) dioxane, water, 20 min

6: 89 percent / pyridine / 1 h

7: 96 percent / NaOMe / methanol; CH₂Cl₂ / 4.5 h

8: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, room temperature, 24 h

9: 53 percent / pyridine / 8 h / Ambient temperature

10: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature

11: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 30 min, 2.) CH₂Cl₂, room temperature, 45 min

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; ethanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen bromide; hydrogen; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; mercury dibromide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform;

DOI:10.1016/S0008-6215(97)00249-8

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

octyl 4-O-acetyl-2-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

1,2:5,6-diacetone-D-glucose

3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

Downstream raw materials:

α-D-Manp-(1->3)-(α-D-Manp)-(1->6)-β-D-Manp-1->O(CH2)7CH3

Refernces