2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene

Base Information

• Chemical Name: 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene
• CAS No.: 314754-14-8
• Molecular Formula: C₈₇H₉₈O₁₂S
• Molecular Weight: 1367.79
• Mol file: 314754-14-8.mol

Synonyms:2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene

Chemical Property of 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene

There total 5 articles about 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene 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: 93.0%

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol (72174-24-4,53269-97-9) + 2,7-di-tert-butyl-4-chloromethyl-9,9-dimethyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene (314754-63-7) → 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene (314754-14-8)

Guidance literature:

With 15-crown-5; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1002/1099-0690(200011)2000:21<3527::aid-ejoc3527>3.3.co;2-g

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene (314754-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / 15-crown-5; NaH / tetrahydrofuran / 2 h / 20 °C

2: 93 percent / NaH; 15-crown-5 / dimethylformamide / 20 h / 20 °C

With 15-crown-5; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Condensation / 2: Condensation;

DOI:10.1002/1099-0690(200011)2000:21<3527::aid-ejoc3527>3.3.co;2-g

Reference yield:

2,7-di-t-butyl-9,9-dimethyl-4,5-xanthenedicarboxylic acid (130525-39-2) → 2,7-di-tert-butyl-9,9-dimethyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopranosylthio)methyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene (314754-14-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 9 percent / borane*dimethyl sulfide / tetrahydrofuran / 4 h / Heating

2: 91 percent / SOCl₂ / CH₂Cl₂ / 2 h / 20 °C

3: 64 percent / 15-crown-5; NaH / tetrahydrofuran / 2 h / 20 °C

4: 93 percent / NaH; 15-crown-5 / dimethylformamide / 20 h / 20 °C

With thionyl chloride; 15-crown-5; dimethylsulfide borane complex; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Substitution / 3: Condensation / 4: Condensation;

DOI:10.1002/1099-0690(200011)2000:21<3527::aid-ejoc3527>3.3.co;2-g

upstream raw materials:

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol

2,7-di-tert-butyl-4-chloromethyl-9,9-dimethyl-5-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yloxy)methylxanthene

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

2,7-di-t-butyl-9,9-dimethyl-4,5-xanthenedicarboxylic acid

Downstream raw materials:

methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside