N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Base Information

Chemical Name:N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
CAS No.:187173-20-2
Molecular Formula:C₅₇H₇₆N₄O₁₅
Molecular Weight:1057.25
Hs Code.:

N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Chemical Property of N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Technology Process of N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

There total 13 articles about N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 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:

: 125631-33-6,125647-51-0,132871-89-7,132871-95-5,132871-96-6,123487-65-0
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol

: 187173-20-2
N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 13 steps

1: 46 percent / PPTS / dimethylformamide / 24 h

2: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) DMF, 100 deg C, 20 min

3: 81 percent / pyridine / Ambient temperature

4: 85 percent / NaBH₃CN, mol. sieves 3A, TFA / dimethylformamide / 48 h / 0 - 20 °C

5: 90 percent / NaH / dimethylformamide / 3 h / -15 °C

6: 87 percent / DDQ / CH₂Cl₂; H₂O / 5 h / Ambient temperature

7: 100 percent / pyridine / 7 h / Ambient temperature

8: 90 percent / NaN₃ / dimethylformamide / 32 h / 20 - 40 °C

9: 48 percent / NIS, AgOTf / CH₂Cl₂ / 20 h / Ambient temperature

10: 96 percent / MeONa / methanol / 36 h / Ambient temperature

11: 73 percent / AgOTf, mol. sieves 4A, collidine / CH₂Cl₂ / 4 h / -40 - 20 °C

12: ethylenediamine / butan-1-ol / 14 h / 70 °C

13: Et₃N / methanol / 12 h / Ambient temperature

With pyridine; 2,3,5-trimethyl-pyridine; N-iodo-succinimide; sodium azide; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; ethylenediamine; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1016/S0968-0896(96)00180-0

Reference yield:

: 118249-72-2
octyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

: 187173-20-2
N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 48 percent / NIS, AgOTf / CH₂Cl₂ / 20 h / Ambient temperature

2: 96 percent / MeONa / methanol / 36 h / Ambient temperature

3: 73 percent / AgOTf, mol. sieves 4A, collidine / CH₂Cl₂ / 4 h / -40 - 20 °C

4: ethylenediamine / butan-1-ol / 14 h / 70 °C

5: Et₃N / methanol / 12 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; N-iodo-succinimide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; ethylenediamine; triethylamine; In methanol; dichloromethane; butan-1-ol;
DOI:10.1016/S0968-0896(96)00180-0

Reference yield:

: 187173-19-9
C₆₉H₈₂N₄O₁₉

: 187173-20-2
N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: ethylenediamine / butan-1-ol / 14 h / 70 °C

2: Et₃N / methanol / 12 h / Ambient temperature

With ethylenediamine; triethylamine; In methanol; butan-1-ol;
DOI:10.1016/S0968-0896(96)00180-0