prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside

Base Information

• Chemical Name: prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside
• CAS No.: 131267-21-5
• Molecular Formula: C₄₉H₅₄O₁₀
• Molecular Weight: 802.962
• Mol file: 131267-21-5.mol

Synonyms:prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside

Chemical Property of prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside

There total 8 articles about prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside 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: 80.0%

(2S,3R,4R,5S,6R)-2-((2R,3R,4S,5R)-2-Allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (130136-33-3) → prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside (131267-21-5)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 60 ℃; for 2h;

DOI:10.1016/0008-6215(90)80143-Q

Reference yield:

allyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-β-D-xylopyranoside (130177-82-1) → prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside (131267-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1: MeONa / methanol

2: 80 percent / potassium tert-butoxide / dimethylsulfoxide / 2 h / 60 °C

With potassium tert-butylate; sodium methylate; In methanol; dimethyl sulfoxide;

DOI:10.1016/0008-6215(90)80143-Q

Reference yield:

benzyl bromide (100-39-0) → prop-1-enyl 3,4-di-O-benzyl-2-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylopyranoside (131267-21-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium hydride / 1.) N,N-dimethylformamide, 2 h, room temperature, 2.) 12 h

2: 2,6-dimethylpyridinium perchlorate / 1,2-dichloro-ethane; chlorobenzene / 40 h / 85 °C

3: 2 M sodium methoxide / methanol / 1 h / Ambient temperature

4: 83 percent / silver triflate, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

5: MeONa / methanol

6: 80 percent / potassium tert-butoxide / dimethylsulfoxide / 2 h / 60 °C

With 4 A molecular sieve; potassium tert-butylate; sodium methylate; silver trifluoromethanesulfonate; 2,6-lutidinium perchlorate; sodium hydride; In methanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; chlorobenzene;

DOI:10.1016/0008-6215(90)80143-Q

upstream raw materials:

(2S,3R,4R,5S,6R)-2-((2R,3R,4S,5R)-2-Allyloxy-4,5-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

allyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-β-D-xylopyranoside

benzyl bromide

(3aR,6R,7S,7aR)-2-Ethoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Downstream raw materials:

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

C₇₃H₈₆O₂₆

2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-D-xylopyranose

2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-α-D-xylopyranosyl bromide