(2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol
CAS No.:299403-77-3
Molecular Formula:C₂₂H₂₈O₅
Molecular Weight:372.461
Hs Code.:

Synonyms:(2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

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Chemical Property of (2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

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Technology Process of (2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

There total 1 articles about (2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-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: 80.0%

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 299403-76-2
(2R,3S,6R)-6-Allyl-3-(1-ethoxy-ethoxy)-2-prop-2-ynyl-3,6-dihydro-2H-pyran

: 299403-77-3
(2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: (2R,3S,6R)-6-Allyl-3-(1-ethoxy-ethoxy)-2-prop-2-ynyl-3,6-dihydro-2H-pyran; With n-butyllithium; In tetrahydrofuran;

3-(p-methoxybenzyloxy)propanal; In methanol;
DOI:10.1016/S0040-4039(00)00988-6

Reference yield:

: 617-86-7
triethylsilane

: 299403-77-3
(2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

: 1026611-82-4
{(2R,4aS,6R,9aR)-2-Allyl-6-[2-(4-methoxy-benzyloxy)-ethyl]-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-8-yl}-triethyl-silane

Guidance literature:: (2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol; Co₂(CO)8; In dichloromethane;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃;

triethylsilane; In toluene; at 70 ℃;
DOI:10.1016/S0040-4039(00)00988-6

Reference yield:

: 299403-77-3
(2R,3S,6R)-6-Allyl-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-3,6-dihydro-2H-pyran-3-ol

: 299403-91-1
Benzoic acid (2R,4aS,6R,7S,9aR)-2-allyl-6-((Z)-pent-2-en-4-ynyl)-4a,6,7,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: CH₂Cl₂

1.2: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

1.3: toluene / 70 °C

2.1: DDQ

3.1: Jones reagent

4.1: I(collidine)2PF₆ / CH₂Cl₂

5.1: DIBAL

6.1: DBU

7.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

8.1: 80 percent / BF₃*OEt₂ / CH₂Cl₂

9.1: 100 percent / TBAF / tetrahydrofuran

10.1: 100 percent / PPh₃; DEAD

With n-butyllithium; jones reagent; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1.1: Addition / 1.2: Cyclization / 1.3: hydrosilylation / 2.1: Oxidation / 3.1: Oxidation / 4.1: lactonization / 5.1: Epoxidation / 6.1: Reduction / 7.1: Peterson olefination / 8.1: Reduction / 9.1: desilylation / 10.1: Mitsunobu reaction;
DOI:10.1016/S0040-4039(00)00988-6