(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

Base Information

Chemical Name:(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol
CAS No.:481725-15-9
Molecular Formula:C₁₇H₂₂O₆
Molecular Weight:322.358
Hs Code.:

Synonyms:(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

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Chemical Property of (S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

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Technology Process of (S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

There total 1 articles about (S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol 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%

: 2675-79-8
1-bromo-3,4,5-trimethoxybenzene

: (1S,2R,6R,7R)-4,10-Dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-ol

: 481725-15-9
(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

Guidance literature:: 1-bromo-3,4,5-trimethoxybenzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h;

With triisopropoxytitanium(IV) chloride; In diethyl ether; hexane; pentane; at -40 - 0 ℃;

(1S,2R,6R,7R)-4,10-Dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-ol; In tetrahydrofuran; diethyl ether; various solvents; at 0 - 20 ℃; for 4.5h;
DOI:10.1016/S0957-4166(02)00334-8

Reference yield: 78.0%

: 481725-15-9
(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

: 481725-16-0
(1R,2S,5S,6R,7S)-5-[(3',4',5')-trimethoxyphenyl]-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-3-one

Guidance literature:: With tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1016/S0957-4166(02)00334-8

Reference yield:

: 481725-15-9
(S)-((1S,2S,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-(3,4,5-trimethoxy-phenyl)-methanol

: 135947-75-0,143445-03-8
MK 287

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / 4 Angstroem molecular sieves; 4-methoxymorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 5 h / 20 °C

2.1: t-BuLi / pentane / 0.5 h / -78 °C

2.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C

3.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 °C

4.1: 67 percent / 450 °C / 0 Torr

5.1: 75 percent / H₂ / Pt/C / ethyl acetate / atmospheric pressure

6.1: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

7.1: 85 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

With dichloro-acetic acid; tetrapropylammonium perruthennate; NMO; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; platinum on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; pentane;
DOI:10.1016/S0957-4166(02)00334-8