(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester
CAS No.:123074-56-6
Molecular Formula:C₃₃H₅₄O₉
Molecular Weight:594.786
Hs Code.:

(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

Synonyms:(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

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Chemical Property of (2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

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Technology Process of (2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

There total 5 articles about (2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl 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:

: 123074-51-1
(2S,3R,4R,6R)-7,7-(ethylenedithio)-3,4-(isopropylidenedioxy)-2,4,6-trimethylnonanol

: 123074-56-6
(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / NBS / acetone; H₂O / 0.25 h / 0 °C

2: 1.) (COCl)2, Me₂SO, 2.) Et₃N / CH₂Cl₂, 0.5 h, -60 deg C to room temp.

3: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -90 °C

4: 2.) LiN(SiMe₃)2 / 2.) THF, 3 h, -78 deg C

5: 1.) O₃, Sudan III, 2.) Et₃N / 1.) -95 deg C, 2.) CH₂Cl₂, Ac₂O, 0 deg C to room temp., 45 min

With N-Bromosuccinimide; oxalyl dichloride; oil scarlet; boron trifluoride diethyl etherate; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In dichloromethane; water; acetone;
DOI:10.1021/ja00201a066

Reference yield:

: 123074-52-2
(4R,6R,7R,8S)-9-hydroxy-6,7-(isopropylidenedioxy)-4,6,8-trimethylnonan-3-one

: 123074-56-6
(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) (COCl)2, Me₂SO, 2.) Et₃N / CH₂Cl₂, 0.5 h, -60 deg C to room temp.

2: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -90 °C

3: 2.) LiN(SiMe₃)2 / 2.) THF, 3 h, -78 deg C

4: 1.) O₃, Sudan III, 2.) Et₃N / 1.) -95 deg C, 2.) CH₂Cl₂, Ac₂O, 0 deg C to room temp., 45 min

With oxalyl dichloride; oil scarlet; boron trifluoride diethyl etherate; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1021/ja00201a066

Reference yield:

: 123074-53-3
(2R,3R,4R,6R)-3,4-(isopropylidenedioxy)-2,4,6-trimethyl-7-oxononanal

: 123074-56-6
(2R,3S,4S)-4-[(4R,5R)-5-((2R,4R,5S,6R)-7-Benzyloxymethoxy-5-hydroxy-2,4,6-trimethyl-3-oxo-nonyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -90 °C

2: 2.) LiN(SiMe₃)2 / 2.) THF, 3 h, -78 deg C

3: 1.) O₃, Sudan III, 2.) Et₃N / 1.) -95 deg C, 2.) CH₂Cl₂, Ac₂O, 0 deg C to room temp., 45 min

With oil scarlet; boron trifluoride diethyl etherate; ozone; triethylamine; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1021/ja00201a066