3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate

Base Information

• Chemical Name: 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate
• CAS No.: 135593-74-7
• Molecular Formula: C₁₇H₁₉NO₆S
• Molecular Weight: 365.407
• Mol file: 135593-74-7.mol

Synonyms:3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate

Chemical Property of 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate

There total 2 articles about 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate 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: 53.0%

potassium cyanide (151-50-8) + 3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl bromide (135593-78-1) → 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate (135593-74-7) + 3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl thiocyanate (135593-73-6) + 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl isothiocyanate

Guidance literature:

With 18-crown-6 ether; In acetone; at -40 - -35 ℃; for 2.5h; Yields of byproduct given;

DOI:10.1016/0008-6215(91)84047-I

Reference yield:

1,3,4-tri-O-acetyl-2-O-benzyl-L-arabinopyranose (68977-82-2,135681-67-3,135681-68-4) → 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate (135593-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetyl bromide, MeOH / CH₂Cl₂ / 0.58 h

2: 53 percent / 18-crown-6 / acetone / 2.5 h / -40 - -35 °C

With methanol; 18-crown-6 ether; Acetyl bromide; In dichloromethane; acetone;

DOI:10.1016/0008-6215(91)84047-I

Reference yield: 77.0%

3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate (135593-74-7) → methyl 2,3,4-tri-O-acetyl-6-O-(3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl)-α-D-glucopyranoside (135644-27-8) + 3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl isothiocyanate + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6)

Guidance literature:

With methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside; triphenylmethyl perchlorate; In dichloromethane; at -5 ℃; for 3h;

DOI:10.1016/0008-6215(91)84047-I

upstream raw materials:

potassium cyanide

3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl bromide

1,3,4-tri-O-acetyl-2-O-benzyl-L-arabinopyranose

Downstream raw materials:

methyl 2,3,4-tri-O-acetyl-6-O-(3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl)-α-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester

1,3,4,6-tetra-O-acetyl-2-O-(2,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl)-α-D-galactopyranose

penta-O-acetyl-α-D-galactopyranose

Refernces