Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid

Base Information

• Chemical Name: Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid
• CAS No.: 76404-36-9
• Molecular Formula: C₂₁H₂₆O₇
• Molecular Weight: 390.433
• Mol file: 76404-36-9.mol

Synonyms:Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid

Chemical Property of Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid

There total 8 articles about Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid 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: 46.0%

Benzyl-2,3-anhydro-6-desoxy-α-L-talopyranosid (76404-34-7) + 3,4-di-O-acetyl-6-deoxy-L-glucal (34819-86-8) → Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid (76404-36-9)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; for 1h; Ambient temperature;

DOI:10.1002/cber.19801131107

Reference yield:

Benzyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid (76404-30-3) → Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid (76404-36-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / pyridine / 48 h / 5 °C

2: dimethylformamide / 20 h / 95 °C

3: 1 N NaOMe / methanol / 20 h / Ambient temperature

4: 50 percent / 30percent H₂O₂, PhCN, NaHCO₃ / methanol / 72 h / Ambient temperature; further reagent: MeCN

5: 46 percent / 1percent BF₃*Et₂O / toluene / 1 h / Ambient temperature

With boron trifluoride diethyl etherate; dihydrogen peroxide; sodium methylate; sodium hydrogencarbonate; benzonitrile; In pyridine; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1002/cber.19801131107

Reference yield:

phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (76404-29-0) → Benzyl-2,3-anhydro-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-6-desoxy-α-L-talopyranosid (76404-36-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / 1 N NaOMe / methanol / 15 h / Ambient temperature

2: 81 percent / pyridine / 48 h / 5 °C

3: dimethylformamide / 20 h / 95 °C

4: 1 N NaOMe / methanol / 20 h / Ambient temperature

5: 50 percent / 30percent H₂O₂, PhCN, NaHCO₃ / methanol / 72 h / Ambient temperature; further reagent: MeCN

6: 46 percent / 1percent BF₃*Et₂O / toluene / 1 h / Ambient temperature

With boron trifluoride diethyl etherate; dihydrogen peroxide; sodium methylate; sodium hydrogencarbonate; benzonitrile; In pyridine; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1002/cber.19801131107

upstream raw materials:

Benzyl-2,3-anhydro-6-desoxy-α-L-talopyranosid

3,4-di-O-acetyl-6-deoxy-L-glucal

Benzyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid

phenylmethyl 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside

Downstream raw materials:

Benzyl-2-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hexopyranosyl)-3,6-didesoxy-α-L-lyxo-hexopyranosid

Benzyl-2-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosyl)-3,6-didesoxy-3-iod-α-L-idopyranosid