(1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-selena-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-selena-bicyclo[3.2.1]octane-3,4-diol
• CAS No.: 257925-82-9
• Molecular Formula: C₄₁H₄₅NO₇Se
• Molecular Weight: 742.771
• Mol file: 257925-82-9.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-selena-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-selena-bicyclo[3.2.1]octane-3,4-diol

There total 6 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-selena-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:

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside (257925-66-9) → (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-selena-bicyclo[3.2.1]octane-3,4-diol (257925-82-9)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂; AcCl / 10 percent Pd-C / ethyl acetate; methanol / 6 h

2: pyridine / 2.5 h / 0 - 20 °C

3: 77 percent / HBr / acetic acid / 48 h / 20 °C

4: 76 percent / NaBH₄; Se / ethanol; dimethylformamide

5: 83 percent / NaOMe / methanol / 0 °C

6: butan-1-ol / 60 h / 100 °C

With pyridine; selenium; sodium tetrahydroborate; hydrogen bromide; hydrogen; sodium methylate; acetyl chloride; palladium on activated charcoal; In methanol; ethanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; butan-1-ol; 1: Hydrogenolysis / 2: Esterification / 3: Substitution / 4: Cyclization / 5: Epoxidation / 6: Addition;

DOI:10.1071/CH99030

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-episeleno-β-D-galactopyranose (257925-67-0) → (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-selena-bicyclo[3.2.1]octane-3,4-diol (257925-82-9)

Guidance literature:

In butan-1-ol; at 100 ℃; for 60h;

DOI:10.1071/CH99030

Reference yield:

2,3-di-O-acetyl-4,6-di-O-methylsulfonyl-α-D-glucopyranosyl bromide (178319-23-8) → (1S,2S,3S,4R,5S)-2-((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-8-oxa-6-selena-bicyclo[3.2.1]octane-3,4-diol (257925-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / NaBH₄; Se / ethanol; dimethylformamide

2: 83 percent / NaOMe / methanol / 0 °C

3: butan-1-ol / 60 h / 100 °C

With selenium; sodium tetrahydroborate; sodium methylate; In methanol; ethanol; N,N-dimethyl-formamide; butan-1-ol; 1: Cyclization / 2: Epoxidation / 3: Addition;

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-episeleno-β-D-galactopyranose

acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside

2,3-di-O-acetyl-4,6-di-O-methylsulfonyl-α-D-glucopyranosyl bromide

Downstream raw materials:

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