(1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane
• CAS No.: 219854-48-5
• Molecular Formula: C₂₆H₂₆O₄S
• Molecular Weight: 434.556
• Mol file: 219854-48-5.mol

Synonyms:(1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane

Chemical Property of (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane

There total 7 articles about (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-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: 95.0%

Methanesulfonic acid (2S,3S,4R,5S)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester → (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane (219854-48-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1080/15257779908041546

Reference yield:

Acetic acid (3R,4S,5S)-4-benzyloxy-5-benzyloxymethyl-5-methanesulfonyloxymethyl-2-methoxy-tetrahydro-furan-3-yl ester (219854-44-1) → (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane (219854-48-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / TMS-Tf / CH₂Cl₂

2: NH₃ / methanol

3: 95 percent / NaH / dimethylformamide

With ammonia; sodium hydride; trimethyl((trifluoromethyl)sulfonyl)silane; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Cyclization;

DOI:10.1080/15257779908041546

Reference yield:

Acetic acid (2S,3R,4S,5S)-4-benzyloxy-5-benzyloxymethyl-5-methanesulfonyloxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-yl ester (219854-46-3) → (1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane (219854-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃ / methanol

2: 95 percent / NaH / dimethylformamide

With ammonia; sodium hydride; In methanol; N,N-dimethyl-formamide; 1: Deacetylation / 2: Cyclization;

DOI:10.1080/15257779908041546

upstream raw materials:

phenylthiotrimethylsilane

Acetic acid (3R,4S,5S)-4-benzyloxy-5-benzyloxymethyl-5-methanesulfonyloxymethyl-2-methoxy-tetrahydro-furan-3-yl ester

Acetic acid (2S,3R,4S,5S)-4-benzyloxy-5-benzyloxymethyl-5-methanesulfonyloxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-yl ester

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Downstream raw materials:

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,7S)-7-(benzyloxy)-1-[(benzyloxy)methyl]-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane