(1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol

Base Information

• Chemical Name: (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol
• CAS No.: 257925-79-4
• Molecular Formula: C₄₁H₄₅NO₇S
• Molecular Weight: 695.877
• Mol file: 257925-79-4.mol

Synonyms:

Chemical Property of (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol

There total 2 articles about (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol 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:

(1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol (128573-02-4) + 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactopyranose (178319-25-0) → (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol (257925-79-4)

Guidance literature:

In butan-1-ol; at 100 ℃; for 60h;

DOI:10.1071/CH99030

Reference yield:

Acetic acid (1S,2S,3R,4R,5S)-4-acetoxy-2-methanesulfonyloxy-8-oxa-6-thia-bicyclo[3.2.1]oct-3-yl ester (178319-24-9) → (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol (257925-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaOMe / methanol / 16 h / 0 °C

2: butan-1-ol / 60 h / 100 °C

With sodium methylate; In methanol; butan-1-ol; 1: Epoxidation / 2: Addition;

DOI:10.1071/CH99030

Reference yield:

benzoyl chloride (98-88-4) + (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-thia-bicyclo[3.2.1]octane-3,4-diol (257925-79-4) → 2-O-benzoyl-1,6-epithio-4-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)cyclohex-2-enyl]amino-1,4,6-trideoxy-β-D-glucopyranose (257925-80-7)

Guidance literature:

With pyridine; dmap; In dichloromethane; at -30 - 0 ℃;

DOI:10.1071/CH99030

upstream raw materials:

(1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol

3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactopyranose

Acetic acid (1S,2S,3R,4R,5S)-4-acetoxy-2-methanesulfonyloxy-8-oxa-6-thia-bicyclo[3.2.1]oct-3-yl ester

Downstream raw materials:

2-O-benzoyl-1,6-epithio-4-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)cyclohex-2-enyl]amino-1,4,6-trideoxy-β-D-glucopyranose

2-O-benzoyl-3,4-O,N-carbonyl-1,6-epithio-4-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)cyclohex-2-enyl]amino-1,4,6-trideoxy-β-D-glucopyranose