Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 174810-44-7
• Molecular Formula: C₃₀H₄₁N₃O₁₂
• Molecular Weight: 635.668
• Mol file: 174810-44-7.mol

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester

There total 5 articles about Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-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: 50.0%

(1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8) + 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aS,4R,5R,6R,6aS)-6-benzyloxymethyl-2-dimethylamino-5-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-4-yloxy)-tetrahydro-pyran-4-yl ester + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester (174810-44-7)

Guidance literature:

With trifluorormethanesulfonic acid; In nitromethane; toluene; at 60 ℃; for 2h; Yields of byproduct given;

DOI:10.1016/0040-4039(95)02230-9

Reference yield:

<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol (134756-63-1) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester (174810-44-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / NaH / 5 h / -78 deg C to room temp.

2: 1.) mercury(II)trifluoroacetate, 2.) O₂, 1M NaBH₄, 2M NaOH / 1.) THF, room temp., 36 h, 2.) 1,4-dioxane, room temp., 2 h

3: 90 percent / 1N HF / acetonitrile / 18 h / Ambient temperature

4: 50 percent / TfOH / nitromethane; toluene / 2 h / 60 °C

With sodium hydroxide; sodium tetrahydroborate; trifluorormethanesulfonic acid; hydrogen fluoride; oxygen; mercury(II) trifluoroacetate; sodium hydride; In nitromethane; toluene; acetonitrile;

DOI:10.1016/0040-4039(95)02230-9

Reference yield:

<1R-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethysilyl)oxy>-1-O-(dimethylamidino)-2-cyclopentene (174810-41-4) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester (174810-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) mercury(II)trifluoroacetate, 2.) O₂, 1M NaBH₄, 2M NaOH / 1.) THF, room temp., 36 h, 2.) 1,4-dioxane, room temp., 2 h

2: 90 percent / 1N HF / acetonitrile / 18 h / Ambient temperature

3: 50 percent / TfOH / nitromethane; toluene / 2 h / 60 °C

With sodium hydroxide; sodium tetrahydroborate; trifluorormethanesulfonic acid; hydrogen fluoride; oxygen; mercury(II) trifluoroacetate; In nitromethane; toluene; acetonitrile;

DOI:10.1016/0040-4039(95)02230-9

upstream raw materials:

(1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol

<1R-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethysilyl)oxy>-1-O-(dimethylamidino)-2-cyclopentene