2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

Base Information

Chemical Name:2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid
CAS No.:185671-89-0
Molecular Formula:C₅₁H₆₈O₉
Molecular Weight:825.096
Hs Code.:

Synonyms:2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

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Chemical Property of 2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

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Technology Process of 2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

There total 9 articles about 2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid 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: 84.0%

: 185671-88-9
5-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

: 185671-89-0
2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

Guidance literature:: With potassium hydroxide; In dimethyl sulfoxide; isopropyl alcohol; at 60 ℃; for 4h;
DOI:10.1016/S0040-4020(96)00950-7

Reference yield:

: 154714-19-9
5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

: 185671-89-0
2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / pyridine / 0.17 h / 0 °C

2: 1.) <9-H-9-BBN>2, 2.) NaOMe, 3.) KBr, PdCl₂(dppf)

3: 92 percent / Bu₄NF / tetrahydrofuran / Ambient temperature

4: MS 3A / silver silicate on alumina / CH₂Cl₂ / 0.5 h / 0 °C

5: NaBH₄ / CH₂Cl₂; methanol / 4 h / -78 - 20 °C

6: 84 percent / aq. KOH / dimethylsulfoxide; propan-2-ol / 4 h / 60 °C

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; sodium tetrahydroborate; 9-BBN dimer; tetrabutyl ammonium fluoride; sodium methylate; potassium bromide; silver silicate on alumina; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; isopropyl alcohol;
DOI:10.1016/S0040-4020(96)00950-7

Reference yield:

: 185671-83-4
(2R)-heptadec-16-enol

: 185671-89-0
2-[(R)-16-((2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-heptadecyl]-6-hydroxy-benzoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / imidazole / dimethylformamide / Ambient temperature

2: 1.) <9-H-9-BBN>2, 2.) NaOMe, 3.) KBr, PdCl₂(dppf)

3: 92 percent / Bu₄NF / tetrahydrofuran / Ambient temperature

4: MS 3A / silver silicate on alumina / CH₂Cl₂ / 0.5 h / 0 °C

5: NaBH₄ / CH₂Cl₂; methanol / 4 h / -78 - 20 °C

6: 84 percent / aq. KOH / dimethylsulfoxide; propan-2-ol / 4 h / 60 °C

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; sodium tetrahydroborate; 9-BBN dimer; tetrabutyl ammonium fluoride; sodium methylate; potassium bromide; silver silicate on alumina; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/S0040-4020(96)00950-7