Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester

Base Information

• Chemical Name: Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester
• CAS No.: 1053611-11-2
• Molecular Formula: C₄₃H₅₃NO₁₃
• Molecular Weight: 791.893

Synonyms:

Chemical Property of Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester

There total 9 articles about Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl 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:

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside (144685-11-0) → Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester (1053611-11-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) NaH, 15-crown-5 / 1) DMF, RT, 30 min, 2) DMF, 70 deg C, 25 h

2: 90 percent / DMSO, Ac₂O / 18 h / Ambient temperature

3: 81 percent / DBU / toluene / 1 h / 80 °C

4: 44 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

5: 97 percent / pyridine / 2 h / Ambient temperature

6: 60percent aq. AcOH / 11 h / 55 °C

7: pyridine / 5 h / Ambient temperature

8: 1) H₂O, 2) pyridine / 1) DMF, 120 deg C, 3 d, 2) RT, 5 h

With pyridine; sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; water; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; toluene;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

N-((2R,3R,4R,6R)-4-Benzyloxy-6-benzyloxymethyl-2-methoxy-5-oxo-tetrahydro-pyran-3-yl)-acetamide → Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester (1053611-11-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 27 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

2: 1) NaH, 15-crown-5 / 1) DMF, RT, 30 min, 2) DMF, 70 deg C, 25 h

3: 90 percent / DMSO, Ac₂O / 18 h / Ambient temperature

4: 81 percent / DBU / toluene / 1 h / 80 °C

5: 44 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

6: 97 percent / pyridine / 2 h / Ambient temperature

7: 60percent aq. AcOH / 11 h / 55 °C

8: pyridine / 5 h / Ambient temperature

9: 1) H₂O, 2) pyridine / 1) DMF, 120 deg C, 3 d, 2) RT, 5 h

With pyridine; sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; water; acetic anhydride; L-Selectride; sodium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2R,4aR,6R,8S,8aR)-8-benzyloxy-7-oxo-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (208524-41-8) → Acetic acid (1S,2S,3S,4R,6R)-3-acetoxy-4-acetoxymethyl-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-cyclohexyl ester (1053611-11-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 44 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

2: 97 percent / pyridine / 2 h / Ambient temperature

3: 60percent aq. AcOH / 11 h / 55 °C

4: pyridine / 5 h / Ambient temperature

5: 1) H₂O, 2) pyridine / 1) DMF, 120 deg C, 3 d, 2) RT, 5 h

With pyridine; sodium tetrahydroborate; cerium(III) chloride; water; acetic acid; In methanol; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

upstream raw materials:

sodium acetate

acetic anhydride

Acetic acid (1S,2R,3R,4R,6R)-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-benzyloxy-3-methanesulfonyloxy-4-methanesulfonyloxymethyl-cyclohexyl ester

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

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