(2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:241129-80-6
Molecular Formula:C₃₄H₄₄N₄O₁₃
Molecular Weight:716.742
Hs Code.:

(2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 18 articles about (2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl 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:

: 118711-49-2
1,2,4,6-tetra-O-acetyl-3-O-benzyl-L-idopyranoside

: 241129-80-6
(2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 61 percent / piperidine / acetic acid; tetrahydrofuran

2: Cs₂CO₃ / CH₂Cl₂

3: BF₃*OEt₂; MS₄A / CH₂Cl₂

4: NaOMe

5: CSA; Me₂C(OMe)2

6: DMAP; pyridine / CH₂Cl₂

7: H₂O / acetic acid

8: TEMPO; NaClO; n-Bu₄NCl / KBr

10: 80 percent / TBDMSOTf; MS₄A / toluene

11: DBU / CH₂Cl₂

With piperidine; pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; tetrabutyl-ammonium chloride; water; sodium methylate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,2-dimethoxy-propane; potassium bromide; In tetrahydrofuran; dichloromethane; acetic acid; toluene; 1: Deacetylation / 2: Addition / 3: Condensation / 4: Deacetylation / 5: acetal formation / 6: Acetylation / 7: Hydrolysis / 8: Oxidation / 9: Esterification / 10: Condensation / 11: Elimination;
DOI:10.1016/S0040-4039(99)01084-9

Reference yield:

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

: 241129-80-6
(2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: Cs₂CO₃ / CH₂Cl₂

2: BF₃*OEt₂; MS₄A / CH₂Cl₂

3: NaOMe

4: CSA; Me₂C(OMe)2

5: DMAP; pyridine / CH₂Cl₂

6: H₂O / acetic acid

7: TEMPO; NaClO; n-Bu₄NCl / KBr

9: 80 percent / TBDMSOTf; MS₄A / toluene

10: DBU / CH₂Cl₂

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; tetrabutyl-ammonium chloride; water; sodium methylate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,2-dimethoxy-propane; potassium bromide; In dichloromethane; acetic acid; toluene; 1: Addition / 2: Condensation / 3: Deacetylation / 4: acetal formation / 5: Acetylation / 6: Hydrolysis / 7: Oxidation / 8: Esterification / 9: Condensation / 10: Elimination;
DOI:10.1016/S0040-4039(99)01084-9

Reference yield:

: 256348-52-4
2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

: 241129-80-6
(2R,3S,4S,5R,6R)-5-Acetoxy-3-((2R,3R,4R,5S,6R)-6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-amino-ethoxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: BF₃*OEt₂; MS₄A / CH₂Cl₂

2: NaOMe

3: CSA; Me₂C(OMe)2

4: DMAP; pyridine / CH₂Cl₂

5: H₂O / acetic acid

6: TEMPO; NaClO; n-Bu₄NCl / KBr

8: 80 percent / TBDMSOTf; MS₄A / toluene

9: DBU / CH₂Cl₂

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; tetrabutyl-ammonium chloride; water; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,2-dimethoxy-propane; potassium bromide; In dichloromethane; acetic acid; toluene; 1: Condensation / 2: Deacetylation / 3: acetal formation / 4: Acetylation / 5: Hydrolysis / 6: Oxidation / 7: Esterification / 8: Condensation / 9: Elimination;
DOI:10.1016/S0040-4039(99)01084-9