(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane
• CAS No.: 434342-92-4
• Molecular Formula: C₃₂H₃₈O₄S
• Molecular Weight: 518.717
• Mol file: 434342-92-4.mol

Synonyms:(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane

Chemical Property of (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane

There total 13 articles about (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane 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: 77.0%

diphenyldisulfane (882-33-7) + ((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-methanol (434342-79-7) → (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane (434342-92-4)

Guidance literature:

With pyridine; tributylphosphine; at 20 ℃;

DOI:10.1055/s-2002-19778

Reference yield:

benzyl bromide (100-39-0) → (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane (434342-92-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / aq. AcOH / 60 °C

2: 85 percent / aq. NaIO₄ / methanol / 20 °C

3: 98 percent / NaBH₄ / methanol / 0 °C

4: 77 percent / Bu₃P; pyridine / 20 °C

With pyridine; sodium tetrahydroborate; sodium periodate; tributylphosphine; acetic acid; In methanol;

DOI:10.1055/s-2002-19778

Reference yield:

ethyl (1R,2S,3R,4S)-3-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-5-oxobicyclo[2.2.1]heptane-2-carboxylate (213816-61-6) → (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane (434342-92-4)

Guidance literature:

Multi-step reaction with 6 steps

1: DIBALH / tetrahydrofuran / -78 °C

2: 91 percent / aq. AcOH / 60 °C

3: 85 percent / aq. NaIO₄ / methanol / 20 °C

4: 98 percent / NaBH₄ / methanol / 0 °C

5: 77 percent / Bu₃P; pyridine / 20 °C

With pyridine; sodium tetrahydroborate; sodium periodate; tributylphosphine; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1055/s-2002-19778

upstream raw materials:

diphenyldisulfane

((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-methanol

benzyl bromide

ethyl (1R,2S,3R,4S)-3-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-5-oxobicyclo[2.2.1]heptane-2-carboxylate

Downstream raw materials:

(1R,2R,3R,4S,5S)-3-Benzenesulfinylmethyl-5-benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-bicyclo[2.2.1]heptane