Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:337356-42-0
Molecular Formula:C₁₉H₁₉NO₉
Molecular Weight:405.361
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl 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: 65.0%

: 613-90-1
benzoyl cyanide

: 3150-24-1
4-nitrophenyl-β-D-galactopyranoside

: 337356-42-0
Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multistep reaction;
DOI:10.1016/S0960-894X(00)00611-9

Reference yield: 55.0%

: 116450-06-7
methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate^10,13

: 337356-42-0
Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

: 337356-43-1
(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3S,4S,5R,6S)-2-benzoyloxymethyl-3,5-dihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; In dichloromethane; acetonitrile; at -45 - -20 ℃; for 4h;
DOI:10.1016/S0960-894X(00)00611-9

Reference yield:

: 337356-42-0
Benzoic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

: (2S,4S,5R,6R)-5-Acetylamino-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 55 percent / NIS; TfOH; 3 Angstroem molecular sieve / CH₂Cl₂; acetonitrile / 4 h / -45 - -20 °C

2: 100 percent / NaOMe; MeOH / 20 h / 0 °C

With methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; sodium methylate; In dichloromethane; acetonitrile;
DOI:10.1016/S0960-894X(00)00611-9