O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Base Information

• Chemical Name: O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride
• CAS No.: 115435-52-4
• Molecular Formula: C₅₁H₅₄ClFO₁₂
• Molecular Weight: 913.434
• Mol file: 115435-52-4.mol

Synonyms:

Chemical Property of O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

There total 4 articles about O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 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:

Chloro-acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester (115435-51-3) → O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (115435-52-4)

Guidance literature:

With silver fluoride; In acetonitrile; at 20 ℃; for 16h; Yield given;

DOI:10.1016/0008-6215(87)80246-X

Reference yield:

allyl O-(2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (115435-47-7) → O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (115435-52-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / pyridine / 4 h / 20 °C

2: 86 percent / PdCl₂, NaOAc / acetic acid; H₂O / 2 h / 50 °C

3: SOCl₂ / 1,2-dichloro-ethane; dimethylformamide / 19 h / 20 °C

4: AgF / acetonitrile / 16 h / 20 °C

With pyridine; thionyl chloride; sodium acetate; silver fluoride; palladium dichloride; In water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(87)80246-X

Reference yield:

O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-D-glucopyranose → O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (115435-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 1,2-dichloro-ethane; dimethylformamide / 19 h / 20 °C

2: AgF / acetonitrile / 16 h / 20 °C

With thionyl chloride; silver fluoride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(87)80246-X

upstream raw materials:

Chloro-acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

allyl O-(2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

Chloro-acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chloro-acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-((2R,3R,4S)-4,5-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

allyl O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl-<(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl>3-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

allyl O-(4-O-acetyl-2,3-di-O-benzyl-6-O-monochloroacetyl-α-D-glucopyranosyl)-<(1->4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl>4-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside