Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 854971-12-3
• Molecular Formula: C₂₂H₃₅NO₆
• Molecular Weight: 409.523
• Mol file: 854971-12-3.mol

Synonyms:Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

There total 1 articles about Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-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:

(3S,4R,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate (762261-99-4) → Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester (854971-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc dichloride etherate / CH₂Cl₂ / Heating

2.1: O₃; Me₂S / CH₂Cl₂ / -78 °C

2.2: 86 percent / DIBALH / toluene / -40 °C

With dimethylsulfide; ozone; zinc(II) chloride; In dichloromethane;

DOI:10.1016/j.tetlet.2005.04.041

Reference yield: 86.0%

Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester (854971-12-3) + acetic anhydride (108-24-7) → Acetic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-3-diisopropylcarbamoyloxy-6-methoxy-tetrahydro-pyran-4-yl ester (854971-17-8)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1016/j.tetlet.2005.04.041

Reference yield:

Diisopropyl-carbamic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester (854971-12-3) → Acetic acid (2R,3S,4S,6R)-6-allyl-2-((S)-1-benzyloxy-ethyl)-3-diisopropylcarbamoyloxy-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / DMAP; pyridine / 20 °C

2: 92 percent / TMSOTf / acetonitrile / -40 - 0 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1016/j.tetlet.2005.04.041

upstream raw materials:

(3S,4R,5S)-5-(benzyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)hex-1-en-3-yl diisopropylcarbamate

Downstream raw materials:

Acetic acid (2R,3S,4S,6R)-2-((S)-1-benzyloxy-ethyl)-3-diisopropylcarbamoyloxy-6-methoxy-tetrahydro-pyran-4-yl ester