(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol
CAS No.:200621-39-2
Molecular Formula:C₃₅H₃₄O₅
Molecular Weight:534.652
Hs Code.:

Synonyms:(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

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Chemical Property of (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

There total 4 articles about (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-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: 86.0%

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 4440-01-1
lithium phenylacetylide

: 200621-39-2
(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

Guidance literature:: lithium phenylacetylide; With zinc(II) chloride;

3,4,6-tri-O-benzyl-D-glucal epoxide; In dichloromethane; at 0 - 20 ℃; for 5h;
DOI:10.1055/s-2003-38751

Reference yield: 82.0%

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 536-74-3
phenylacetylene

: 200621-39-2
(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

Guidance literature:: phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.333333h;

With triisopropoxytitanium(IV) chloride; In tetrahydrofuran; hexane; at -50 ℃; for 0.25h;

3,4,6-tri-O-benzyl-D-glucal epoxide; In tetrahydrofuran; hexane; at -50 - -20 ℃;
DOI:10.1081/CAR-120026458

Reference yield:

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 536-74-3
phenylacetylene

: 200621-43-8
(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)(phenyl)ethyne

: 200621-39-2
(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(phenylethynyl)tetrahydro-2H-pyran-3-ol

Guidance literature:: phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.333333h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

3,4,6-tri-O-benzyl-D-glucal epoxide; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃;
DOI:10.1081/CAR-120026458