(2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol
• CAS No.: 156943-36-1
• Molecular Formula: C₂₂H₂₉NO₉
• Molecular Weight: 451.474
• Mol file: 156943-36-1.mol

Synonyms:

Chemical Property of (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol

There total 3 articles about (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol 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:

Acetic acid (2S,3S,4S,5R)-4,5-diacetoxy-2-[(R)-5-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3-yl ester (156943-35-0) → (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol (156943-36-1)

Guidance literature:

With potassium cyanide; In methanol;

DOI:10.1016/S0040-4039(00)76857-2

Reference yield:

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) → (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol (156943-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene di-isocyanate, Et₃N / toluene / 10 h / Heating

2: KCN / methanol

With potassium cyanide; triethylamine; 2,4-Toluene diisocyanate; In methanol; toluene;

DOI:10.1016/S0040-4039(00)76857-2

Reference yield:

2,3,4-tri-O-acetyl-β-D-xylopyranosyl(nitro)methane (113972-89-7) → (2S,3R,4S,5R)-2-[(R)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3,4,5-triol (156943-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene di-isocyanate, Et₃N / toluene / 10 h / Heating

2: KCN / methanol

With potassium cyanide; triethylamine; 2,4-Toluene diisocyanate; In methanol; toluene;

DOI:10.1016/S0040-4039(00)76857-2

upstream raw materials:

Acetic acid (2S,3S,4S,5R)-4,5-diacetoxy-2-[(R)-5-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4,5-dihydro-isoxazol-3-yl]-tetrahydro-pyran-3-yl ester

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

2,3,4-tri-O-acetyl-β-D-xylopyranosyl(nitro)methane

Downstream raw materials:

(R)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-1-((2R,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-propan-1-one