phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

Base Information

• Chemical Name: phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside
• CAS No.: 158780-52-0
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 158780-52-0.mol

Synonyms:phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

Chemical Property of phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

There total 1 articles about phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside 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: 95.0%

(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-50-8) → phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside (158780-52-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0040-4039(00)76001-1

Reference yield: 99.0%

chloromethyl methyl ether (107-30-2) + phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside (158780-52-0) → (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole (161099-08-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;

Reference yield:

phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside (158780-52-0) → (1S,5R,6R,7R)-1-Allyl-6-benzyloxy-5-methoxymethoxymethyl-2,8-dioxa-bicyclo[3.2.1]octan-7-ol

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / iPr₂NEt / CH₂Cl₂

2: 1.) OsO₄, NMO; 2.) NaIO₄; 3.) NaBH₄ / 1.) THF, H₂O; 3.) EtOH

3: 98 percent / imidazole / dimethylformamide

4: Li / liquid ammonia

5: 1.) CCl₄; 2.) Li / 1.) HMPT, THF; 2.) liq. NH₃

6: NaH / dimethylformamide; tetrahydrofuran

7: 2,2-dimethyldioxirane / acetone; CH₂Cl₂ / 0 °C

8: 0.5 h / Ambient temperature

9: 76 percent / NaH / dimethylformamide; tetrahydrofuran

10: 1.) 1,4-diazabicyclo<2.2.2>octane; 2.) Hg(OAc)2 / 1.) (Ph₃P)3RhCl / 1.) EtOH, 2 h, reflux; 2.) THF, H₂O

11: 2.) Dess-Martin periodinane / 1.) THF

12: 89 percent / 50 percent HF / acetonitrile; H₂O / 2.5 h / Ambient temperature

13: DDQ / CH₂Cl₂; H₂O

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; tetrachloromethane; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2-dimethyldioxirane; hydrogen fluoride; mercury(II) diacetate; lithium; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; ammonia; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4039(00)76001-1

upstream raw materials:

(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Downstream raw materials:

(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-propenyl)-α-D-lyxofuranoside

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-acetyloxy-3-phenylthiopropyl)-α-D-lyxofuranoside