3,6-di-O-benzyl-L-galactal

Base Information

• Chemical Name: 3,6-di-O-benzyl-L-galactal
• CAS No.: 692740-51-5
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392

Synonyms:

Chemical Property of 3,6-di-O-benzyl-L-galactal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-di-O-benzyl-L-galactal

There total 13 articles about 3,6-di-O-benzyl-L-galactal 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:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → 3,6-di-O-benzyl-L-galactal (692740-51-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 85 percent / camphor sulfonic acid / tetrahydrofuran / 12 h / 85 °C

2.1: 82 percent / NaH / dimethylformamide / 48 h / 20 °C

3.1: 82 percent / lithium naphthalenide / tetrahydrofuran / -78 °C

4.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

5.1: 80 percent / CuI / tetrahydrofuran / 0.33 h / -10 °C

6.1: 2.25 g / KOH; H₂O₂ / tetrahydrofuran; methanol / 18 h / 20 °C

7.1: (n-Bu)2SnO / toluene / 2 h / Heating

7.2: 94 percent / tetrabutylammonium iodide; triethylamine / toluene / 18 h / Heating

8.1: 96 percent / acetic acid / tetrahydrofuran; H₂O / 2 h / 45 °C

9.1: tetramethyl-1-piperidine oxide; NaClO; NaHCO₃ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

10.1: 0.99 g / N,N-dimethylformamide dineopentyl acetate / xylene / 1 h / 75 - 150 °C

11.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

12.1: NaBH₄ / CH₂Cl₂; methanol / 1.5 h / -5 °C

With potassium hydroxide; sodium hypochlorite; sodium tetrahydroborate; copper(l) iodide; tetramethyl-1-piperidine oxide; camphor-10-sulfonic acid; dihydrogen peroxide; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; naphthalen-1-yl-lithium; N,N-dimethylformamide dineopentyl acetal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene; 6.1: Tamao-Kumada oxidation;

DOI:10.1021/jo035789l

Reference yield:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → 3,6-di-O-benzyl-L-galactal (692740-51-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 99 percent / NaOMe / methanol; CH₂Cl₂ / 1 h / 0 °C

2.1: 85 percent / camphor sulfonic acid / tetrahydrofuran / 12 h / 85 °C

3.1: 82 percent / NaH / dimethylformamide / 48 h / 20 °C

4.1: 82 percent / lithium naphthalenide / tetrahydrofuran / -78 °C

5.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

6.1: 80 percent / CuI / tetrahydrofuran / 0.33 h / -10 °C

7.1: 2.25 g / KOH; H₂O₂ / tetrahydrofuran; methanol / 18 h / 20 °C

8.1: (n-Bu)2SnO / toluene / 2 h / Heating

8.2: 94 percent / tetrabutylammonium iodide; triethylamine / toluene / 18 h / Heating

9.1: 96 percent / acetic acid / tetrahydrofuran; H₂O / 2 h / 45 °C

10.1: tetramethyl-1-piperidine oxide; NaClO; NaHCO₃ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

11.1: 0.99 g / N,N-dimethylformamide dineopentyl acetate / xylene / 1 h / 75 - 150 °C

12.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

13.1: NaBH₄ / CH₂Cl₂; methanol / 1.5 h / -5 °C

With potassium hydroxide; sodium hypochlorite; sodium tetrahydroborate; copper(l) iodide; tetramethyl-1-piperidine oxide; camphor-10-sulfonic acid; dihydrogen peroxide; sodium methylate; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; naphthalen-1-yl-lithium; N,N-dimethylformamide dineopentyl acetal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene; 7.1: Tamao-Kumada oxidation;

DOI:10.1021/jo035789l

Reference yield:

3*,6*-di-O-benzyl-L-glucal (547763-60-0) → 3,6-di-O-benzyl-L-galactal (692740-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

2: NaBH₄ / CH₂Cl₂; methanol / 1.5 h / -5 °C

With sodium tetrahydroborate; sodium hydrogencarbonate; Dess-Martin periodane; In methanol; dichloromethane;

DOI:10.1021/jo035789l

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

3*,6*-di-O-benzyl-L-glucal

3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucal

Downstream raw materials:

3,4,6-tri-O-benzyl-L-galactal

methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside

Acetic acid (2R,3S,4R,5R,6S)-2-{(2S,3R,4S,5S,6S)-5-(acetyl-benzenesulfonyl-amino)-4-benzyloxy-2-benzyloxymethyl-6-[2-(4-methoxy-benzyloxy)-ethoxy]-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

ethyl 4-O-(2-acetyl-3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phenylsulfonamido-1-thio-β-L-glucopyranoside

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