Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester
CAS No.:220662-78-2
Molecular Formula:C₂₁H₂₅BrO₁₀
Molecular Weight:517.327
Hs Code.:

Synonyms:Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester 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: 67.0%

: 18982-54-2
o-bromobenzyl alcohol

: 121238-27-5
2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

: 220662-78-2
Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1021/jo971778e

Reference yield:

: 220662-78-2
Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

: (2S,3S,4S,5S,6R)-2-(2-Bromo-benzyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 1h;
DOI:10.1021/jo971778e

Reference yield:

: 220662-78-2
Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(2-bromo-benzyloxy)-tetrahydro-pyran-4-yl ester

: 220662-70-4
methyl 4-{1-[2-(((2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy)methyl)phen-1-yl]vinyl}-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOMe / methanol / 1 h / 20 °C

2.1: 7.41 g / NaH; tetra-n-butylammonium iodide / dimethylformamide / 16 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -100 °C

3.2: 94 percent / tetrahydrofuran; hexane / 0.5 h / -100 °C

4.1: 77 percent / DMAP; DCC / CH₂Cl₂ / 16 h / 0 - 20 °C

5.1: 80 percent / tetrahydrofuran; toluene / 3.5 h / 0 - 20 °C

With dmap; n-butyllithium; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Deacetylation / 2.1: Alkylation / 3.1: Metallation / 3.2: Carboxylation / 4.1: Esterification / 5.1: Condensation;
DOI:10.1021/jo971778e