(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

Chemical Name:(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
CAS No.:756496-88-5
Molecular Formula:C₃₆H₄₂O₁₁
Molecular Weight:650.723
Hs Code.:

(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Chemical Property of (2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Technology Process of (2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 9 articles about (2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-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:

: 756496-87-4
benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-3-O-benzyl-2,6-di-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside

: 756496-88-5
(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -30 - 20 ℃;
DOI:10.1002/ejoc.200300807

Reference yield:

: 100-39-0
benzyl bromide

: 756496-88-5
(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 630 mg / NaH / dimethylformamide / 5 h

2: nBu₄NF / tetrahydrofuran / -30 - 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300807

Reference yield:

: (2S,3R,4S,5R,6R)-2-((3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

: 756496-88-5
(2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-((2R,3R,4R,5R,6R)-4,6-bis-benzyloxy-5-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: Bu₂SnO / methanol / 15 h / 60 °C

1.2: 11.84 g / Bu₄NI / toluene / 17 h / 60 °C

2.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

3.1: camphorsulfonic acid / acetonitrile / 0.5 h

4.1: 3.35 g / collidine / dimethylformamide / 20 °C

5.1: NaOH / ethanol / 40 °C

6.1: 630 mg / NaH / dimethylformamide / 5 h

7.1: nBu₄NF / tetrahydrofuran / -30 - 20 °C

With 2,3,5-trimethyl-pyridine; sodium hydroxide; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200300807