Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

Base Information

Chemical Name:Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester
CAS No.:207681-90-1
Molecular Formula:C₂₆H₃₇NO₁₄
Molecular Weight:587.578
Hs Code.:

Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

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Chemical Property of Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

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Technology Process of Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

There total 5 articles about Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl 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: 42.0%

: 108-24-7
acetic anhydride

: 207681-89-8
methyl 4,6-dideoxy-4-[(1'R,4'R,5'S,6'S)-4',5',6'-trihydroxy-3'-(hydroxymethyl)cyclohex-2'-enyl]amino-β-D-glucopyranoside

: 2106-10-7
1-deoxy-1-fluoro-α-D-glucose

: Acetic acid (1S,2R,5R,6S)-6-acetoxy-3-acetoxymethyl-5-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-3-enyl ester

: acetic acid 3-acetoxy-6-acetoxymethyl-2-[5,6-diacetoxy-2-acetoxymethyl-4-(4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-2-enyloxy]-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

: 207681-90-1
Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

Guidance literature:: methyl 4,6-dideoxy-4-[(1'R,4'R,5'S,6'S)-4',5',6'-trihydroxy-3'-(hydroxymethyl)cyclohex-2'-enyl]amino-β-D-glucopyranoside; 1-deoxy-1-fluoro-α-D-glucose; With AbgGlu₃₅₈Ser glycosynthase; ammonium bicarbonate; In water; at 20 ℃; for 72h;

acetic anhydride; With pyridine;
DOI:10.1071/CH03203

Reference yield:

: 39946-32-2
methyl 2-O-benzyl-6-deoxy-β-D-galactopyranoside

: 207681-90-1
Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 59 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -50 °C

2: 83 percent / pyridine / CH₂Cl₂ / -20 - 0 °C

3: 43 percent / 1,3-dimethylimidazolidin-2-one / 120 h / Ambient temperature

4: 1.) sodium metal, 2.) lithium metal / 1.) methanol, 30 min, 2.) THF, liq. NH₃, -75 deg C, 1h, 3.) pyridine

With pyridine; 1,3-dimethyl-2-imidazolidinone; dmap; sodium; lithium; triethylamine; In dichloromethane;
DOI:10.1071/C97153

Reference yield:

: 207602-70-8
methyl 3-O-benzoyl-2-O-benzyl-6-deoxy-β-D-galactopyranoside

: 207681-90-1
Acetic acid (1S,2R,5R,6S)-5,6-diacetoxy-4-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-ylamino)-cyclohex-3-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / pyridine / CH₂Cl₂ / -20 - 0 °C

2: 43 percent / 1,3-dimethylimidazolidin-2-one / 120 h / Ambient temperature

3: 1.) sodium metal, 2.) lithium metal / 1.) methanol, 30 min, 2.) THF, liq. NH₃, -75 deg C, 1h, 3.) pyridine

With pyridine; 1,3-dimethyl-2-imidazolidinone; sodium; lithium; In dichloromethane;
DOI:10.1071/C97153