(2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Base Information

Chemical Name:(2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
CAS No.:571146-93-5
Molecular Formula:C₃₄H₃₂O₉
Molecular Weight:584.623
Hs Code.:

Synonyms:(2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

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Chemical Property of (2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

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Technology Process of (2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

There total 3 articles about (2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one 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: 66.0%

: 100-39-0
benzyl bromide

: 79595-97-4
norbergenin

: 571146-93-5
(2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; acetone; at 20 ℃; for 24h;
DOI:10.1016/S0968-0896(02)00666-1

Reference yield:

: (2R,3R,4R,4aS,10bS)-3,4,8-Triacetoxy-2-acetoxymethyl-9-hydroxy-6-oxo-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene-10-carboxylic acid methyl ester

: 571146-93-5
(2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1.89 g / K₂CO₃ / H₂O / 1 h

2: 66 percent / K₂CO₃ / dimethylformamide; acetone / 24 h / 20 °C

With potassium carbonate; In water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0968-0896(02)00666-1

Reference yield:

: bergenin pentaacetate

: 571146-93-5
(2R,3S,4S,4aR,10bS)-8,9,10-Tris-benzyloxy-3,4-dihydroxy-2-hydroxymethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Guidance literature:: Multi-step reaction with 3 steps

1: BCl₃ / CH₂Cl₂ / 0 - 20 °C

2: 1.89 g / K₂CO₃ / H₂O / 1 h

3: 66 percent / K₂CO₃ / dimethylformamide; acetone / 24 h / 20 °C

With boron trichloride; potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0968-0896(02)00666-1