(2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 192505-52-5
• Molecular Formula: C₂₉H₄₀Cl₃NO₁₂
• Molecular Weight: 700.995

Synonyms:(2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property of (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 10 articles about (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl 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: 87.0%

trichloroacetonitrile (545-06-2) + (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-6-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester → (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (192505-52-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1016/S0960-894X(97)00252-7

Reference yield:

2,4,6-tri-O-acetate-3-O-methyl-α-D-glucopyranosylbromide (30694-94-1) → (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (192505-52-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / NaBH₄ / ethanol; CH₂Cl₂ / Heating

2: 94 percent / MeONa / methanol / Ambient temperature

3: 88 percent / APTS / acetonitrile / Ambient temperature

4: 1.) BuLi, 2.) imidazole / 1.) THF, 2.) THF

5: 1.) Bu₃SnH, AIBN, 2.) 40percent aq. HF / 1.) toluene, 2.) THF

7: 86 percent / Et₃N, DMAP / CH₂Cl₂

8: 93 percent / NaH / dimethylformamide

10: 87 percent / DBU / CH₂Cl₂

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(97)00252-7

Reference yield:

phenyl 3-O-Methyl-1-seleno-β-D-glucopyranoside (202648-26-8) → (2S,3S,4S,5R)-3-((2R,3S,4R,5R,6R)-6-Acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (192505-52-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / APTS / acetonitrile / Ambient temperature

2: 1.) BuLi, 2.) imidazole / 1.) THF, 2.) THF

3: 1.) Bu₃SnH, AIBN, 2.) 40percent aq. HF / 1.) toluene, 2.) THF

5: 86 percent / Et₃N, DMAP / CH₂Cl₂

6: 93 percent / NaH / dimethylformamide

8: 87 percent / DBU / CH₂Cl₂

With 1H-imidazole; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(97)00252-7

upstream raw materials:

trichloroacetonitrile

2,4,6-tri-O-acetate-3-O-methyl-α-D-glucopyranosylbromide

phenyl 3-O-Methyl-1-seleno-β-D-glucopyranoside

phenyl 2,4,6-tri-O-Acetyl-3-O-methyl-1-seleno-β-D-glucopyranoside

Downstream raw materials:

(2S,3S,4S,5R,6R)-6-((1R,2R,3S,4R,5R)-3-Acetoxy-4-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-3-((2R,3S,4R,5R,6R)-6-acetoxymethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethyl)-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

C₄₆H₆₀Cl₃NO₁₉

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