Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

Base Information

Chemical Name:Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester
CAS No.:57800-48-3
Molecular Formula:C₁₆H₂₀O₆
Molecular Weight:308.331
Hs Code.:

Synonyms:Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

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Chemical Property of Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

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Technology Process of Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

There total 13 articles about Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl 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: 91.0%

: 98-88-4
benzoyl chloride

: 57800-51-8
2-Hydroxy-1-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-ethanone

: 57800-48-3
Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

Guidance literature:: With pyridine; at 0 ℃; for 10h;
DOI:10.1139/v80-429

Reference yield:

: 33647-80-2
methyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

: 57800-48-3
Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 11.5 g / pyridine / CH₂Cl₂ / 18 h

2: sodium iodide / butan-2-one / 17 h / Ambient temperature

3: 92 percent / Raney nickel / acetone / 18 h / Heating

4: 1.) potassium tert-butoxide, 2.)lithium aluminum hydride / 1.) dimethylformamide, 0 deg. C, 1 h, 2.) diethyl ether, 0 deg. C, 0.5 h

5: 1.) pyridine, 2.) osmium tetroxide / 1.)methylene chloride, 18h, 2.) pyridine, 24 h

6: 1.)dimethyl sulphoxide, trifluoroacetic acid, N,N'-dicyclohexilcarbodiimiide / benzene; pyridine / 2.5 h

7: hydrogen chloride / CHCl₃ / -30 °C

8: 91 percent / pyridine / 10 h / 0 °C

With pyridine; hydrogenchloride; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; nickel; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; In pyridine; dichloromethane; chloroform; acetone; butanone; benzene;
DOI:10.1139/v80-429

Reference yield:

: 50895-52-8
methyl 2,3,6-trideoxy-α-D-glycero-hexopyranosid-4-ulose

: 57800-48-3
Benzoic acid 2-((2R,3S,6S)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-2-oxo-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) potassium tert-butoxide, 2.)lithium aluminum hydride / 1.) dimethylformamide, 0 deg. C, 1 h, 2.) diethyl ether, 0 deg. C, 0.5 h

2: 1.) pyridine, 2.) osmium tetroxide / 1.)methylene chloride, 18h, 2.) pyridine, 24 h

3: 1.)dimethyl sulphoxide, trifluoroacetic acid, N,N'-dicyclohexilcarbodiimiide / benzene; pyridine / 2.5 h

4: hydrogen chloride / CHCl₃ / -30 °C

5: 91 percent / pyridine / 10 h / 0 °C

With pyridine; hydrogenchloride; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; chloroform; benzene;
DOI:10.1139/v80-429