Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

Base Information

Chemical Name:Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester
CAS No.:237075-32-0
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

Synonyms:Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

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Chemical Property of Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

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Technology Process of Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

There total 13 articles about Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl 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: 77.0%

: 237075-31-9
Benzoic acid (3R,4S,5S,6R)-4-((E)-4-hydroxy-1-methyl-but-1-enyl)-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

: 237075-32-0
Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid;
DOI:10.1021/ja990784k

Reference yield:

: 237075-23-9
2,2-dimethyl-4-(3-methylbut-3-enyl)[1,3]dioxolane

: 237075-32-0
Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1: Br₂, KHMDS / diethyl ether / -78 °C

2: 1.) O₃, 2.) Ph₃P

3: KOH

4: 1.) t-BuLi, Bu₃SnLi, 3.) n-BuLi, CuCN,

6: MCPBA

7: TBAF, NH₄Cl

8: Ag₂O

9: L-selectride

11: H₂O, H(+)

12: 1.) NaIO₄, 2.) <(Me)3S=O>(+), NaH

13: 77 percent / MCPBA

With potassium hydroxide; sodium periodate; n-butyllithium; tri-n-butyltin lithium; trimethylsulfoxonium ion; tetrabutyl ammonium fluoride; water; bromine; tert.-butyl lithium; hydrogen cation; potassium hexamethylsilazane; L-Selectride; sodium hydride; ammonium chloride; ozone; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; silver(l) oxide; In diethyl ether;
DOI:10.1021/ja990784k

Reference yield:

: 237075-22-8
(S)-2,2-Dimethyl-1,3-dioxa-spiro[4.5]dec-6-en-8-one

: 237075-32-0
Benzoic acid (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxy-ethyl)-2-methyl-oxiranyl]-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) t-BuLi, Bu₃SnLi, 3.) n-BuLi, CuCN,

3: MCPBA

4: TBAF, NH₄Cl

5: Ag₂O

6: L-selectride

8: H₂O, H(+)

9: 1.) NaIO₄, 2.) <(Me)3S=O>(+), NaH

10: 77 percent / MCPBA

With sodium periodate; n-butyllithium; tri-n-butyltin lithium; trimethylsulfoxonium ion; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; hydrogen cation; L-Selectride; sodium hydride; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide;
DOI:10.1021/ja990784k