acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose

Base Information

• Chemical Name: acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose
• CAS No.: 865859-84-3
• Molecular Formula: C₂₈H₃₂O₁₀S
• Molecular Weight: 560.622
• Mol file: 865859-84-3.mol

Synonyms:acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose

Chemical Property of acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose

There total 6 articles about acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose 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: 71.0%

acetic acid (1S)-1-phenyl-2-(phenylsulfanyl)ethyl ester (865860-14-6) + 1,3,4,6-tetra-O-acetyl glucopyranose (4692-12-0) → acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose (865859-84-3)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ja052548h

Reference yield: 62.0%

(2S,4aS,6R,7R,8S,8aR)-6-acetoxymethyl-7,8-diacetoxy-2-phenylhexahydro-4aH-pyrano[3,2-b][1,4]oxathiine + lead(IV) tetraacetate (546-67-8) + 1H-1,2,3-benzotriazol-1-amine (1614-12-6) → acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose (865859-84-3)

Guidance literature:

In dichloromethane; at -78 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.3762/bjoc.6.19

Reference yield:

(S)-Mandelic acid (17199-29-0) → acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose (865859-84-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / LiAlH₄ / diethyl ether / 2 h / Heating

2: 88 percent / Bu₂SnO; Et₃N / CH₂Cl₂ / 3 h / 20 °C

3: 98 percent / tetrahydrofuran / 20 °C

4: 82 percent / pyridine / 2 h / 0 °C

5: 71 percent / BF₃*OEt₂; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; lithium aluminium tetrahydride; 4 A molecular sieve; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja052548h

upstream raw materials:

acetic acid (1S)-1-phenyl-2-(phenylsulfanyl)ethyl ester

1,3,4,6-tetra-O-acetyl glucopyranose

(S)-Mandelic acid

(S)-1-phenyl-1,2-ethanediol

Downstream raw materials:

3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate