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

Base Information

Chemical Name: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
CAS No.:185671-88-9
Molecular Formula:C₅₄H₇₂O₉
Molecular Weight:865.16
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 185671-87-8
5-[(R)-16-((2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-heptadecyl]-2,2-dimethyl-benzo[1,3]dioxin-4-one

: 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

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 20 ℃; for 4h; Yield given;
DOI:10.1016/S0040-4020(96)00950-7

Reference yield:

: 158818-92-9
3,4,6-tri-O-benzyl-α-D-arabino-hexopyranose-2-ulosyl bromide

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; silver silicate on alumina; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(96)00950-7