[(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol

Base Information

• Chemical Name: [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol
• CAS No.: 195316-22-4
• Molecular Formula: C₂₄H₃₀O₅S₂
• Molecular Weight: 462.631

Synonyms:[(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol

Chemical Property of [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol

There total 12 articles about [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol 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: 100.0%

(2R,3R,4R,5S)-4-benzyloxy-5-(1,3-dithian-2-yl)-3-(4-methoxybenzyloxy)-2-trityloxymethyltetrahydrofuran (195315-86-7) → [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol (195316-22-4)

Guidance literature:

With DL-10-camphorsulfonic acid; In methanol; dichloromethane; for 12h; Ambient temperature;

DOI:10.1248/cpb.45.1265

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol (195316-22-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

3: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

4: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

5: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

6: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

7: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

8: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

9: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

10: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

11: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; DL-10-camphorsulfonic acid; potassium tert-butylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.45.1265

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → [(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-methanol (195316-22-4)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂SO₄ / methanol / 0.25 h / Ambient temperature

2: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

4: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

5: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

6: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

7: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

8: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

9: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

10: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

11: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

12: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; DL-10-camphorsulfonic acid; sulfuric acid; potassium tert-butylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.45.1265

upstream raw materials:

(2R,3R,4R,5S)-4-benzyloxy-5-(1,3-dithian-2-yl)-3-(4-methoxybenzyloxy)-2-trityloxymethyltetrahydrofuran

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

benzyl chloride

Downstream raw materials:

[(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-ylmethoxy]-tert-butyl-diphenyl-silane

2,2-Dimethyl-propionic acid (4S,5S)-5-((2R,3S,4S,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

2,2-Dimethyl-propionic acid (4S,5S)-5-((4aR,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Toluene-4-sulfonic acid 2-((3aS,4S,5aR,5bS,9aR,10aR,10bR)-2,2,7,7-tetramethyl-octahydro-1,3,5,6,8,10-hexaoxa-cyclopenta[a]fluoren-4-yl)-ethyl ester

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