(8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

Base Information

Chemical Name:(8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one
CAS No.:115352-36-8
Molecular Formula:C₂₃H₃₆O₅
Molecular Weight:392.536
Hs Code.:

Synonyms:(8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

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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 (8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

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Technology Process of (8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

There total 10 articles about (8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-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: 98.0%

: 93635-16-6
(8R,9S)-4-Benzenesulfonyl-10-benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

: 115352-36-8
(8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

Guidance literature:: With aluminium amalgam; In tetrahydrofuran; water; Ambient temperature;
DOI:10.1016/S0040-4039(01)91087-1

Reference yield:

: 93662-86-3
isopropyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside

: 115352-36-8
(8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1) cuprouos iodide / 1) THF, -20 deg C, 10 min, 2)THF, -40 deg C, 30 min; further reag.: cyanocuprate, var. time and temp.

2: hydrazine monohydrate, triethylamine / ethanol / 55 °C

3: sodium dimsylate / dimethylsulfoxide-d6 / 1.5 h / Ambient temperature

4: 1) sodium hydride / 1) THF, DMF, RT, 20 min, 2) THF, DMF, 20 h

5: 1N HCl / tetrahydrofuran; H₂O / 5 h / 55 °C

6: bromine, sodium acetate / H₂O; dimethylformamide / 3 h / Ambient temperature

7: 1) n-butyllithium / 1) THF, -78 to 0 deg C, 2) THF, -78 deg C, 1 h

8: aluminum foil, 2percent aq. mercuric chloride / tetrahydrofuran; H₂O / 24 h / Ambient temperature

With hydrogenchloride; copper(l) iodide; n-butyllithium; bromine; sodium acetate; sodium hydride; sodium methylsulfinylmethanide; hydrazine hydrate; triethylamine; aluminium; mercury dichloride; In tetrahydrofuran; dimethylsulfoxide-d6; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86917-9

Reference yield:

: 3366-47-0
2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose

: 115352-36-8
(8R,9S)-10-Benzyloxy-9-hydroxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-decan-5-one

Guidance literature:: Multi-step reaction with 9 steps

1: 63.1 percent / BF₃*Et₂O / benzene / 0.17 h / Ambient temperature

2: 1) cuprouos iodide / 1) THF, -20 deg C, 10 min, 2)THF, -40 deg C, 30 min; further reag.: cyanocuprate, var. time and temp.

3: hydrazine monohydrate, triethylamine / ethanol / 55 °C

4: sodium dimsylate / dimethylsulfoxide-d6 / 1.5 h / Ambient temperature

5: 1) sodium hydride / 1) THF, DMF, RT, 20 min, 2) THF, DMF, 20 h

6: 1N HCl / tetrahydrofuran; H₂O / 5 h / 55 °C

7: bromine, sodium acetate / H₂O; dimethylformamide / 3 h / Ambient temperature

8: 1) n-butyllithium / 1) THF, -78 to 0 deg C, 2) THF, -78 deg C, 1 h

9: aluminum foil, 2percent aq. mercuric chloride / tetrahydrofuran; H₂O / 24 h / Ambient temperature

With hydrogenchloride; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; bromine; sodium acetate; sodium hydride; sodium methylsulfinylmethanide; hydrazine hydrate; triethylamine; aluminium; mercury dichloride; In tetrahydrofuran; dimethylsulfoxide-d6; ethanol; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(01)86917-9