2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside

Base Information

• Chemical Name: 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside
• CAS No.: 139631-51-9
• Molecular Formula: C₅₆H₆₂O₁₁
• Molecular Weight: 911.102

Synonyms:2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside

Chemical Property of 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside

There total 34 articles about 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside 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:

*,R*)>-diethyl (2E,6E)-4,5-bis(phenylmethoxy)-2,6-octadienedioate (130860-91-2) → 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside (139631-51-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 71 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 18 h / Ambient temperature

2: 100 percent / 2,6-dimethyllutidine / CH₂Cl₂ / 14 h / Ambient temperature

3: 82 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 1.) oxalyl chloride, DMSO / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, -78 deg C, 20 min

5: 82 percent / pyridine / toluene; tetrahydrofuran / 5 h / -78 - -10 °C

6: 95 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

7: 1.) oxalyl chloride, DMSO / 1.) dichlromethane, -78 deg C, 20 min, 2.) dichloromethane, -78 deg C, 1 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, RT, 5 h

9: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

10: 88 percent / concd. H₂SO₄ / 18 h / Ambient temperature

11: 92 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

12: imidazole / dimethylformamide

13: 63 percent / dihydroquinine p-chlorobenzoate, N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O; toluene / Ambient temperature

14: NaH / dimethylformamide / 0 °C

15: tetrabutylammonium fluoride (TBAF) / tetrahydrofuran

16: 97 percent / oxalyl chloride, DMSO

17: 1.) TFA, 2.) TFA / 1.) H₂O, THF, reflux, 2 h, 2.) H₂O, THF, reflux, overnight

With pyridine; 1H-imidazole; 2,6-dimethyllutidine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dihydroquinine 4-chlorobenzoate; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

Reference yield:

*,R*)>-diethyl (2E,6E)-4,5-bis(phenylmethoxy)-2,6-octadienedioate (130860-91-2) → 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-α-undecofuranoside (139631-51-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 71 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 18 h / Ambient temperature

2: 100 percent / 2,6-dimethyllutidine / CH₂Cl₂ / 14 h / Ambient temperature

3: 82 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 1.) oxalyl chloride, DMSO / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, -78 deg C, 20 min

5: 82 percent / pyridine / toluene; tetrahydrofuran / 5 h / -78 - -10 °C

6: 95 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

7: 1.) oxalyl chloride, DMSO / 1.) dichlromethane, -78 deg C, 20 min, 2.) dichloromethane, -78 deg C, 1 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, RT, 5 h

9: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

10: 88 percent / concd. H₂SO₄ / 18 h / Ambient temperature

11: 92 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

12: imidazole / dimethylformamide

13: 63 percent / dihydroquinine p-chlorobenzoate, N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O; toluene / Ambient temperature

14: NaH / dimethylformamide / 0 °C

15: tetrabutylammonium fluoride (TBAF) / tetrahydrofuran

16: 97 percent / oxalyl chloride, DMSO

17: 1.) TFA, 2.) TFA / 1.) H₂O, THF, reflux, 2 h, 2.) H₂O, THF, reflux, overnight

With pyridine; 1H-imidazole; 2,6-dimethyllutidine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dihydroquinine 4-chlorobenzoate; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

Reference yield:

(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate (130860-94-5) → 2-propenyl 2,3,6,7,10,11-hexakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-β-undecofuranoside (139631-51-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

2: imidazole / dimethylformamide

3: 63 percent / dihydroquinine p-chlorobenzoate, N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O; toluene / Ambient temperature

4: NaH / dimethylformamide / 0 °C

5: tetrabutylammonium fluoride (TBAF) / tetrahydrofuran

6: 97 percent / oxalyl chloride, DMSO

7: 1.) TFA, 2.) TFA / 1.) H₂O, THF, reflux, 2 h, 2.) H₂O, THF, reflux, overnight

With 1H-imidazole; osmium(VIII) oxide; oxalyl dichloride; dihydroquinine 4-chlorobenzoate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

(2R,3S)-2,3-Bis-benzyloxy-3-((4R,5R)-5-{(1R,2R)-1,2-bis-benzyloxy-2-[(4R,5R)-5-((R)-1,2-bis-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde

allyl alcohol

*,R^*)>-diethyl (2E,6E)-4,5-bis(phenylmethoxy)-2,6-octadienedioate

(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

Downstream raw materials:

2-propenyl 2,3,5,6,7,8,,9,10,11-nonakis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-α-undecofuranoside

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