(4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane
• CAS No.: 106062-14-0
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 106062-14-0.mol

Synonyms:(4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane

Chemical Property of (4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane

There total 2 articles about (4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane 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: 88.0%

benzyl bromide (100-39-0) + (2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol (106062-13-9) → (4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane (106062-14-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 2h; Heating;

DOI:10.1016/S0040-4039(00)84793-0

Reference yield:

(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde (99603-55-1) → (4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane (106062-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4A molecular sieves / CH₂Cl₂ / 1.) -78 deg C, 2.5 h; 2.) 23 deg C

2: 88 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / Heating

With 4 A molecular sieve; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84793-0

Reference yield: 98.0%

(4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane (106062-14-0) → lyxo-4-O-Benzylhept-1-ene-4,5,6-triol (106062-15-1)

Guidance literature:

With water; acetic acid; at 100 ℃; for 4h;

DOI:10.1016/S0040-4039(00)84793-0

upstream raw materials:

benzyl bromide

(2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol

(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde

Downstream raw materials:

lyxo-4-O-Benzylhept-1-ene-4,5,6-triol

methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

methyl 4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-D-lyxo-hexopyranoside

Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester