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

Base Information

• Chemical Name: 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose
• CAS No.: 19685-14-4
• Molecular Formula: C₁₂H₁₉ClO₅
• Molecular Weight: 278.733
• Mol file: 19685-14-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 6-chloro-O¹,O²;O³,O⁵-diisopropylidene-α-D-6-deoxy-glucofuranose 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: 53.7%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9) + (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose (74925-18-1) + 6-chloro-O1,O2;O3,O5-diisopropylidene-α-D-6-deoxy-glucofuranose (19685-14-4)

Guidance literature:

With 1H-imidazole; N-chloro-succinimide; triphenylphosphine; In chlorobenzene; for 3h; Heating;

DOI:10.1016/0008-6215(92)84042-Q

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:

6-chloro-O1,O2;O3,O5-diisopropylidene-α-D-6-deoxy-glucofuranose (19685-14-4) → (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid (59865-23-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / LiNH₂, liq. NH₃

2: 95 percent / NBS / CH₂Cl₂

3: 80 percent / Bu₃SnH, AIBN / toluene

4: 92 percent / 50percent aq. AcOH / 50 °C

5: 88 percent / PCC, NaOAc / CH₂Cl₂

6: 100 percent / DBU / CH₂Cl₂

7: 95 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 2585.7 Torr

With N-Bromosuccinimide; lithium amide; 2,2'-azobis(isobutyronitrile); ammonia; hydrogen; tri-n-butyl-tin hydride; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; rhodium on alumina; In dichloromethane; ethyl acetate; toluene;

upstream raw materials:

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

Downstream raw materials:

6-chloro-6-deoxy-D-glucose

(3aR,5R,6S,6aR)-5-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

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

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