(1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

Base Information

Chemical Name:(1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate
CAS No.:173911-77-8
Molecular Formula:C₃₁H₃₄O₉
Molecular Weight:550.606
Hs Code.:

Synonyms:(1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

Suppliers and Price of (1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

There total 7 articles about (1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate 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: 53.0%

: 173911-76-7
methyl (Z)-2-O-benzyl-3,4-di-O-(p-methoxybenzyl)-6-O-acetyl-α-D-glucos-5-enopyranoside

: 173911-77-8
(1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

Guidance literature:: With water; palladium dichloride; In 1,4-dioxane; at 60 ℃; for 6h;
DOI:10.1016/S0040-4039(98)02230-8

Reference yield: 53.0%

: Acetic acid (3S,4S,5R,6S)-5-benzyloxy-6-methoxy-3,4-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-(2Z)-ylidenemethyl ester

: 173911-77-8
(1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

Guidance literature:: palladium dichloride; In 1,4-dioxane; water; at 60 ℃; for 8h;
DOI:10.1021/jo001575h

Reference yield:

: 18929-63-0
methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

: 173911-77-8
(1R,2R,3S,4R,5S)-3-benzyloxy-2-hydroxy-4,5-bis(4-methoxybenzyloxy)-6-oxocyclohexyl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 37 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 48 h / Heating

2: 76 percent / NaH / dimethylformamide / 2 h / 50 °C

3: 77 percent / DIBAL-H / CH₂Cl₂ / 1 h / -40 °C

4: 1.) (COCl)2, DMSO, 2.) K₂CO₃ / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) MeCN, reflux, overnight

5: 1.) Hg(OAc)2, 2.) aq. NaCl / 1.) Me₂CO, H₂O, 45 min, 2.) room temperature, 24 h

With sodium hydroxide; oxalyl dichloride; mercury(II) diacetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; sodium chloride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo951057k