(2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol

Base Information

• Chemical Name: (2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol
• CAS No.: 365562-71-6
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• Mol file: 365562-71-6.mol

Synonyms:(2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol

Chemical Property of (2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol

There total 3 articles about (2R,3R)-4-(benzyloxy)-2-allyl-butan-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: 57.0%

vinyl magnesium bromide (1826-67-1) + (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol (78469-85-9,78513-07-2,78513-15-2,84621-89-6,87172-27-8,95672-91-6,98048-62-5,98048-63-6,78513-12-9) → (R)-2-Benzyloxymethyl-but-3-enal + (2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol (365562-71-6)

Guidance literature:

vinyl magnesium bromide; (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at -10 ℃; for 18h;

With sodium periodate; In tetrahydrofuran; water; at 0 ℃; for 4h; pH=2;

DOI:10.1016/S0040-4039(01)01048-6

Reference yield:

(E)-4-(benzyloxy)-2-buten-1-ol (80885-30-9,81028-03-7,69152-88-1) → (2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol (365562-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / Ti(OiPr)4; (+)-DET; t-BuOOH / 18 h / -18 °C

2.1: CuI / tetrahydrofuran; diethyl ether / 18 h / -10 °C

2.2: 57 percent / NaIO₄ / tetrahydrofuran; H₂O / 4 h / 0 °C / pH 2

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2R,3R)-tartrate; In tetrahydrofuran; diethyl ether; 1.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)01048-6

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → (2R,3R)-4-(benzyloxy)-2-allyl-butan-1,3-diol (365562-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate; celite / CH₂Cl₂ / 18 h / 20 °C

1.2: 89 percent / NaBH₄ / methanol / 2 h / -40 °C

2.1: 84 percent / Ti(OiPr)4; (+)-DET; t-BuOOH / 18 h / -18 °C

3.1: CuI / tetrahydrofuran; diethyl ether / 18 h / -10 °C

3.2: 57 percent / NaIO₄ / tetrahydrofuran; H₂O / 4 h / 0 °C / pH 2

With titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2R,3R)-tartrate; Celite; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)01048-6

upstream raw materials:

vinyl magnesium bromide

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol

(E)-4-(benzyloxy)-2-buten-1-ol

(Z)-4-benzyloxy-but-2-en-1-ol

Downstream raw materials:

(2-benzyloxymethyl-but-3-enyloxy)-tert-butyl-diphenyl-silane

(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-pent-4-ene-1,2-diol

2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-en-1-ol