(E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

Base Information

Chemical Name:(E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol
CAS No.:138152-95-1
Molecular Formula:C₂₈H₄₀O₆
Molecular Weight:472.622
Hs Code.:

Synonyms:(E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

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Chemical Property of (E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

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Technology Process of (E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

There total 8 articles about (E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol 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:

: 4799-68-2
3-benzyloxypropan-1-ol

: 138152-95-1
(E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

Guidance literature:: Multi-step reaction with 8 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

2: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> 0 deg C, 19 h

3: DIBAH / CH₂Cl₂ / 1 h / -78 °C

4: L-(+)-diethyl tartrate, titanium isopropoxide, 3-Angstroem molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / -15 °C

5: oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

6: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 10 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> rt

7: 79 percent / DIBAH / diethyl ether; hexane / 0.25 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 3 A molecular sieve; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo00027a022

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 138152-95-1
(E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> 0 deg C, 19 h

2: DIBAH / CH₂Cl₂ / 1 h / -78 °C

3: L-(+)-diethyl tartrate, titanium isopropoxide, 3-Angstroem molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / -15 °C

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

5: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 10 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> rt

6: 79 percent / DIBAH / diethyl ether; hexane / 0.25 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 3 A molecular sieve; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo00027a022

Reference yield:

: (2R,3R)-3-(2-Benzyloxy-ethyl)-2-methyl-oxirane-2-carbaldehyde

: 138152-95-1
(E)-(2R,4S,7R)-9-(Benzyloxy)-4-(hydroxymethyl)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethyl-5-nonen-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 10 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> rt

2: 79 percent / DIBAH / diethyl ether; hexane / 0.25 h / -78 °C

With 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; In diethyl ether; hexane;
DOI:10.1021/jo00027a022