(2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol

Base Information

• Chemical Name: (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol
• CAS No.: 124871-88-1
• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.326
• Mol file: 124871-88-1.mol

Synonyms:

Chemical Property of (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol

There total 1 articles about (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol 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: 42.0%

((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol (76639-80-0) + 4-Methoxybenzyl alcohol (105-13-5) → (2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol (124871-88-1)

Guidance literature:

With titanium(IV) isopropylate; In benzene; for 45h; Ambient temperature;

DOI:10.1248/cpb.37.1155

Reference yield:

(2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol (124871-88-1) → (2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane (87641-44-9,98049-27-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Ac₂O, DMAP, Et₃N, 2.) diisopropyl ethylamine, 3.) 1N NaOH / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, 45 deg C, 8 h, 3.) MeOH, RT, 75 min

2: 97 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 2 h / Ambient temperature

3: various solvent(s) / 96 h / Heating

4: 78 percent / LiAlH₄ / diethyl ether / 1.33 h / -15 - -10 °C

5: 59 percent / m-CPBA / CH₂Cl₂ / 2 h / -20 - -10 °C

6: 87 percent / 1.0M B₂H₆ / tetrahydrofuran; hexamethylphosphoric acid triamide / -14 deg C, RT, 14 h

7: 98 percent / acetic acid; H₂O / 46 h / Ambient temperature

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 3 A molecular sieve; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; diborane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; acetic acid;

DOI:10.1248/cpb.37.1155

Reference yield:

(2S,3R)-3-(4-methoxybenzyloxy)-2-methylpentane-1,2-diol (124871-88-1) → (2R,3R)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-2-methylpentanal (125325-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Ac₂O, DMAP, Et₃N, 2.) diisopropyl ethylamine, 3.) 1N NaOH / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, 45 deg C, 8 h, 3.) MeOH, RT, 75 min

2: 97 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; sodium hydroxide; 3 A molecular sieve; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1248/cpb.37.1155

upstream raw materials:

((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol

4-Methoxybenzyl alcohol

Downstream raw materials:

(2S,3R)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-2-methylpentan-1-ol

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane

(2R,3R)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-2-methylpentanal

(2E,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyhept-2-en-1-ol