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

Base Information

• Chemical Name: Benzyl-2-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hexopyranosyl)-3,6-didesoxy-α-L-lyxo-hexopyranosid
• CAS No.: 76404-38-1
• Molecular Formula: C₂₃H₃₂O₈
• Molecular Weight: 436.502

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

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

Chemical Property:

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

There total 10 articles about Benzyl-2-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hexopyranosyl)-3,6-didesoxy-α-L-lyxo-hexopyranosid 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%

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 (76404-37-0) → Benzyl-2-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hexopyranosyl)-3,6-didesoxy-α-L-lyxo-hexopyranosid (76404-38-1)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; for 12h;

DOI:10.1002/cber.19801131107

Reference yield:

Benzyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid (76404-30-3) → Benzyl-2-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hexopyranosyl)-3,6-didesoxy-α-L-lyxo-hexopyranosid (76404-38-1)

Guidance literature:

Multi-step reaction with 7 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

6: 91 percent / LiI*2H₂O / pyridine / 16 h / 60 °C

7: 71 percent / H₂, NEt₃ / 10percent Pd-C / methanol / 12 h

With boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydrogencarbonate; benzonitrile; triethylamine; lithium iodide; palladium on activated charcoal; 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-O-acetyl-4-O-(4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hexopyranosyl)-3,6-didesoxy-α-L-lyxo-hexopyranosid (76404-38-1)

Guidance literature:

Multi-step reaction with 8 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

7: 91 percent / LiI*2H₂O / pyridine / 16 h / 60 °C

8: 71 percent / H₂, NEt₃ / 10percent Pd-C / methanol / 12 h

With boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydrogencarbonate; benzonitrile; triethylamine; lithium iodide; palladium on activated charcoal; In pyridine; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1002/cber.19801131107

upstream raw materials:

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

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

Benzyl-4-O-methylsulfonyl-2,3-6-tridesoxy-α-L-erythro-hex-2-enopyranosid

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