(2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol

Base Information

• Chemical Name: (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol
• CAS No.: 124871-95-0
• Molecular Formula: C₁₉H₃₂O₆
• Molecular Weight: 356.459
• Mol file: 124871-95-0.mol

Synonyms:(2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol

Chemical Property of (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol

There total 8 articles about (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-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: 87.0%

(2S,3R,4S,5R)-2,4-dimethyl-2,3-epoxy-5(4-methoxybenzyloxy)-4-methoxymethoxyheptan-1-ol (124871-94-9,124987-30-0) → (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol (124871-95-0)

Guidance literature:

With diborane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; -14 deg C, RT, 14 h;

DOI:10.1248/cpb.37.1155

Reference yield:

((2S,3S)-3-ethyl-2-methyloxiran-2-yl)methanol (76639-80-0) → (2S,3R,4S,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol (124871-95-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 42 percent / Ti(iso-PrO)4 / benzene / 45 h / Ambient temperature

2: 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

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

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

5: 78 percent / LiAlH₄ / diethyl ether / 1.33 h / -15 - -10 °C

6: 59 percent / m-CPBA / CH₂Cl₂ / 2 h / -20 - -10 °C

7: 87 percent / 1.0M B₂H₆ / tetrahydrofuran; hexamethylphosphoric acid triamide / -14 deg C, RT, 14 h

With titanium(IV) isopropylate; 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; benzene;

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)-2,4-dimethyl-5-(4-methoxybenzyloxy)-4-methoxymethoxyheptane-1,3-diol (124871-95-0)

Guidance literature:

Multi-step reaction with 6 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

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;

DOI:10.1248/cpb.37.1155

upstream raw materials:

(2S,3R,4S,5R)-2,4-dimethyl-2,3-epoxy-5(4-methoxybenzyloxy)-4-methoxymethoxyheptan-1-ol

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

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

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

Downstream raw materials:

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