1,2-O-ISOPROPYLIDENE-3-S-HYDROXY-4-R-ETHYDINYL TETRAHYDROFURAN

Base Information

• Chemical Name: 1,2-O-ISOPROPYLIDENE-3-S-HYDROXY-4-R-ETHYDINYL TETRAHYDROFURAN
• CAS No.: 127223-28-3
• Molecular Formula: C9H12 O4
• Molecular Weight: 184.192
• Mol file: 127223-28-3.mol

Synonyms:a-D-xylo-Hexofuranose,5,5,6,6-tetradehydro-5,6-dideoxy-1,2-O-(1-methylethylidene)-

Chemical Property of 1,2-O-ISOPROPYLIDENE-3-S-HYDROXY-4-R-ETHYDINYL TETRAHYDROFURAN

Chemical Property:

• PSA: 47.92000
• LogP: -0.14310

Purity/Quality:

99% ^*data from raw suppliers

1,2-O-ISOPROPYLIDENE-3-S-HYDROXY-4-R-ETHYDINYL TETRAHYDROFURAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-O-ISOPROPYLIDENE-3-S-HYDROXY-4-R-ETHYDINYL TETRAHYDROFURAN

There total 3 articles about 1,2-O-ISOPROPYLIDENE-3-S-HYDROXY-4-R-ETHYDINYL TETRAHYDROFURAN 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: 97.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (53167-11-6) → (3aR,5R,6S,6aR)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (127223-28-3)

Guidance literature:

1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose; With potassium carbonate; In methanol; at 0 - 20 ℃; for 0.166667h;

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; In methanol; at 0 - 20 ℃; for 7h;

DOI:10.1039/d0ob00170h

Reference yield: 85.0%

6-chloro-O1,O2;O3,O5-diisopropylidene-α-D-6-deoxy-glucofuranose (19685-14-4) → (3aR,5R,6S,6aR)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (127223-28-3)

Guidance literature:

With lithium amide; ammonia;

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (3aR,5R,6S,6aR)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (127223-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1: various solvent(s)

2: 81 percent / LiNH₂ / liquid ammonia / -33 °C

With lithium amide; In ammonia;

DOI:10.1016/S0040-4039(01)80592-X

upstream raw materials:

6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose

Downstream raw materials:

C₂₂H₂₃NO₆S

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

tert-Butyl-diphenyl-[(R)-3-((3aR,5R,6R,6aR)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butoxy]-silane