dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 504422-53-1
• Molecular Formula: C₆₀H₇₄O₁₀
• Molecular Weight: 955.242

Synonyms:dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 12 articles about dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 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: 67.0%

dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-52-0) → dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-53-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 70 ℃; for 1h;

DOI:10.1016/S0008-6215(02)00294-X

Reference yield:

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside (66854-07-7,103129-55-1,117076-31-0) → dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-53-1)

Guidance literature:

Multi-step reaction with 8 steps

1: NaOMe / methanol / 20 °C

2: p-TsOH*H₂O / dimethylformamide / 4.5 h / 50 °C

3: 10.1 g / NaH / dimethylformamide / 0 - 20 °C

4: 95 percent / BH₃*Et₂O; AlCl₃; molecular sieves / tetrahydrofuran / 21 h / 20 °C

5: 96 percent Turnov_. / NaH; 15-crown-5 / dimethylformamide / 120 h / 70 °C

6: 100 percent / pyridine / 20 °C

7: 98 percent / DMSO; Ac₂O / 11 h / 20 °C

8: 67 percent / DBU / toluene / 1 h / 70 °C

With pyridine; aluminium trichloride; molecular sieve; tetrafluoroboric acid-diethyl ether complex; 15-crown-5; sodium methylate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(02)00294-X

Reference yield:

1-dodecyl alcohol (112-53-8) → dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-53-1)

Guidance literature:

Multi-step reaction with 9 steps

1: silver perchlorate; silver carbonate; molecular sieves / CH₂Cl₂

2: NaOMe / methanol / 20 °C

3: p-TsOH*H₂O / dimethylformamide / 4.5 h / 50 °C

4: 10.1 g / NaH / dimethylformamide / 0 - 20 °C

5: 95 percent / BH₃*Et₂O; AlCl₃; molecular sieves / tetrahydrofuran / 21 h / 20 °C

6: 96 percent Turnov_. / NaH; 15-crown-5 / dimethylformamide / 120 h / 70 °C

7: 100 percent / pyridine / 20 °C

8: 98 percent / DMSO; Ac₂O / 11 h / 20 °C

9: 67 percent / DBU / toluene / 1 h / 70 °C

With pyridine; aluminium trichloride; molecular sieve; tetrafluoroboric acid-diethyl ether complex; 15-crown-5; sodium methylate; silver perchlorate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(02)00294-X

upstream raw materials:

dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside

1-dodecyl alcohol

benzyl bromide

Downstream raw materials:

dodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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