(1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.1^3,7]tricosane

Base Information

• Chemical Name: (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.1^3,7]tricosane
• CAS No.: 213768-27-5
• Molecular Formula: C₆₇H₈₀O₁₄
• Molecular Weight: 1109.36

Synonyms:(1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.1^3,7]tricosane

Chemical Property of (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.1^3,7]tricosane

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Technology Process of (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.1^3,7]tricosane

There total 21 articles about (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.1^3,7]tricosane 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: 60.0%

(2R,3R,5R,6R)-3,5-Bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran (172361-29-4) + methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(hexane-1,6-diyl)-α-D-mannopyranoside (213768-08-2) → (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.13,7]tricosane (213768-27-5)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; toluene; 1.) -45 deg C, 20 min, 2.) 30 min;

DOI:10.1021/jo9806097

Reference yield:

benzyl bromide (100-39-0) → (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.13,7]tricosane (213768-27-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 84 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) o deg C to room temperature

2: 84 percent / 80percent AcOH / 4 h / 80 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1.) MeOH, reflux, 2.5 h, 2.) toluene, 60 deg C, 15 h

4: 84 percent / pyridine / Ambient temperature

5: 84 percent / TBAF / tetrahydrofuran / 6 h / Ambient temperature

6: 88 percent / pyridine / Ambient temperature

7: 95 percent / Na / methanol

8: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

9: 87 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 6 h

10: 38 percent / NaH, Cs₂CO₃ / tetrahydrofuran / 24 h / Heating

11: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H₂O, 30 min

12: 60 percent / NIS, AgOTf / CH₂Cl₂; toluene / 1.) -45 deg C, 20 min, 2.) 30 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9806097

Reference yield:

1,6-hexanediol (629-11-8) → (1S,3R,4R,5S,6S,7R,18R,20S,21S,22R)-4,5,6,22-Tetrakis-benzyloxy-21-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-20-methoxy-2,9,16,19,23-pentaoxa-tricyclo[16.2.2.13,7]tricosane (213768-27-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 52 percent / pyridine; CH₂Cl₂ / Ambient temperature

2: 81 percent / pyridine; CH₂Cl₂ / Ambient temperature

3: 98 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 18 h

4: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

5: 87 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 6 h

6: 38 percent / NaH, Cs₂CO₃ / tetrahydrofuran / 24 h / Heating

7: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H₂O, 30 min

8: 60 percent / NIS, AgOTf / CH₂Cl₂; toluene / 1.) -45 deg C, 20 min, 2.) 30 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; silver trifluoromethanesulfonate; sodium hydride; caesium carbonate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo9806097

upstream raw materials:

(2R,3R,5R,6R)-3,5-Bis-benzyloxy-2-ethylsulfanyl-6-methyl-tetrahydro-pyran

methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(hexane-1,6-diyl)-α-D-mannopyranoside

1,6-hexanediol

6-(triphenylmethyloxy)-1-hexanol

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