Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester

Base Information

• Chemical Name: Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester
• CAS No.: 208524-49-6
• Molecular Formula: C₃₂H₄₆N₂O₁₂
• Molecular Weight: 650.723

Synonyms:

Chemical Property of Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester

There total 7 articles about Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl 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-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (142560-73-4) → Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester (208524-49-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / NaCNBH₃ / tetrahydrofuran / 1 h / Ambient temperature

2: Ac₂O, DMSO / 20 h / Ambient temperature

3: 49 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

4: pyridine / 0.5 h / Ambient temperature

5: NaN₃ / dimethylformamide; H₂O / 32 h / 100 °C

6: 81 percent / hydrogen / 10percent Pd/C / ethanol / 8.5 h / Ambient temperature

7: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

With pyridine; sodium azide; hydrogen; acetic anhydride; L-Selectride; sodium cyanoborohydride; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

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

Reference yield:

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside (144685-11-0) → Acetic acid (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester (208524-49-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Ac₂O, DMSO / 20 h / Ambient temperature

2: 49 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

3: pyridine / 0.5 h / Ambient temperature

4: NaN₃ / dimethylformamide; H₂O / 32 h / 100 °C

5: 81 percent / hydrogen / 10percent Pd/C / ethanol / 8.5 h / Ambient temperature

6: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

With pyridine; sodium azide; hydrogen; acetic anhydride; L-Selectride; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

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 (3aS,4S,5R,7R,7aS)-5-((2S,3S,4S,5R,6R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-6-methoxy-tetrahydro-pyran-3-ylamino)-7-benzyloxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester (208524-49-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 49 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

2: pyridine / 0.5 h / Ambient temperature

3: NaN₃ / dimethylformamide; H₂O / 32 h / 100 °C

4: 81 percent / hydrogen / 10percent Pd/C / ethanol / 8.5 h / Ambient temperature

5: 2) pyridine / 1) isopropanol, 120 deg C, 15 d

With pyridine; sodium azide; hydrogen; L-Selectride; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

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

upstream raw materials:

acetic anhydride

1,2-anhydro-6-O-benzyl-3,4-O-isopropylidene-5a-carba-α-D-galactopyranose

N-((2R,3R,4S,5S,6S)-5-Amino-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-acetamide

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

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

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