(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol
CAS No.:139195-51-0
Molecular Formula:C₅₆H₆₀O₁₀
Molecular Weight:893.086
Hs Code.:

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

There total 12 articles about (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-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: 83.0%

: 139195-50-9
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-3-ol

: 139195-51-0,139242-14-1
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(Z)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

Guidance literature:: With quinoline; hydrogen; Lindlar's catalyst; In ethyl acetate; for 0.333333h; Ambient temperature;
DOI:10.1021/jo00022a039

Reference yield: 77.0%

: 139195-50-9
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-3-ol

: 139195-51-0,139242-14-1
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(E)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; for 0.75h; Ambient temperature;
DOI:10.1021/jo00022a039

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 139195-51-0,139242-14-1
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-[(Z)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, -50 deg C to 0 deg C, 1 min, 2.) THF, -50 deg C, 30 min

2: 69 percent / triethylsilane / BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 0 °C

3: 83 percent / H₂, quinoline / Lindlar catalyst / ethyl acetate / 0.33 h / Ambient temperature

With quinoline; triethylsilane; n-butyllithium; hydrogen; Lindlar's catalyst; boron trifluoride diethyl etherate; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo00022a039