methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside
• CAS No.: 299410-93-8
• Molecular Formula: C₁₇H₂₄O₇
• Molecular Weight: 340.373
• Mol file: 299410-93-8.mol

Synonyms:methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Chemical Property of methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

There total 1 articles about methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside 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: 94.0%

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8) + trimethyleneglycol (504-63-2) → methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside (299410-93-8)

Guidance literature:

With potassium tert-butylate; at 110 ℃; for 14h;

DOI:10.1021/ol006222j

Reference yield: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside (299410-93-8) → methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside (299410-95-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/ol006222j

Reference yield:

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside (299410-93-8) → Eldecalcitol (104121-92-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2.1 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: 91 percent / BaCO₃; NBS / CCl₄ / Heating

3.1: 86 percent / Zn; NaBH₃CN / propan-1-ol; H₂O / 95 °C

4.1: pyridine / 20 °C

5.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

6.2: BF₃*OEt₂ / tetrahydrofuran; hexane / -78 - 20 °C

6.3: 90 percent / K₂CO₃ / methanol / 20 °C

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: 52 percent / Et₃N; Pd(PPh₃)4 / toluene / Heating

9.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrabutyl ammonium fluoride; sodium cyanoborohydride; triethylamine; barium carbonate; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; propan-1-ol; tetrachloromethane; hexane; dichloromethane; water; toluene;

DOI:10.1021/jo0491051

upstream raw materials:

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

trimethyleneglycol

Downstream raw materials:

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside

Eldecalcitol

methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene