1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

Base Information

Chemical Name:1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone
CAS No.:720684-59-3
Molecular Formula:C₅₆H₅₃NO₁₁
Molecular Weight:916.037
Hs Code.:

Synonyms:1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

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Chemical Property of 1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

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Technology Process of 1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

There total 5 articles about 1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone 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: 56.0%

: 18065-05-9
1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

: 720684-58-2
(2R,3R,4S,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-5-(4-nitro-benzyloxy)-tetrahydro-pyran

: 720684-59-3
1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 - 20 ℃;
DOI:10.1016/j.bmcl.2004.03.108

Reference yield:

: 40246-30-8
methyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

: 720684-59-3
1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / 2,4,6-collidine; AgOTf / 35 °C

2: 50 percent / aq. H₂SO₄; AcOH / Heating

3: 78 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / -78 °C

4: 56 percent / BF₃*OEt₂; 4A molecular sieves / CH₂Cl₂ / -20 - 20 °C

With 2,4,6-trimethyl-pyridine; diethylamino-sulfur trifluoride; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; acetic acid; In dichloromethane;
DOI:10.1016/j.bmcl.2004.03.108

Reference yield:

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

: 720684-59-3
1-{4,6-Bis-benzyloxy-3-[(2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-(4-nitro-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-phenyl}-ethanone

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / CH₂Cl₂ / 20 °C

2: 63 percent / 2,4,6-collidine; AgOTf / 35 °C

3: 50 percent / aq. H₂SO₄; AcOH / Heating

4: 78 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / -78 °C

5: 56 percent / BF₃*OEt₂; 4A molecular sieves / CH₂Cl₂ / -20 - 20 °C

With 2,4,6-trimethyl-pyridine; diethylamino-sulfur trifluoride; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; acetic acid; In dichloromethane;
DOI:10.1016/j.bmcl.2004.03.108