methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside
CAS No.:256486-94-9
Molecular Formula:C₃₉H₄₅NO₁₅
Molecular Weight:767.784
Hs Code.:

methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

Synonyms:methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

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Chemical Property of methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

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Technology Process of methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

There total 15 articles about methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside 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:

: Acetic acid (2R,3S,4R,5R,6S)-3-((2R,3R,4S,5S,6R)-3-acetoxy-4-benzyloxy-6-formyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

: 256486-94-9
methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; In tert-butyl alcohol;
DOI:10.1016/S0960-894X(99)00550-8

Reference yield:

: 3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0
2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

: 256486-94-9
methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: HCl

2: CSA / tetrahydrofuran

3: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

4: aq. AcOH

5: pyridine / CH₂Cl₂

6: 75 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

7: NaOMe; MeOH

8: CSA / acetone

9: DMAP; pyridine / CH₂Cl₂

10: aq. AcOH

11: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

12: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

With pyridine; hydrogenchloride; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; barium dihydroxide; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; potassium bromide; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1: Glycosidation / 2: Acetalization / 3: Alkylation / 4: Hydrolysis / 5: Acetylation / 6: Glycosidation / 7: Deacetylation / 8: Acetalization / 9: Acetylation / 10: Hydrolysis / 11: Oxidation / 12: Oxidation;
DOI:10.1016/S0960-894X(99)00550-8

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 256486-94-9
methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 13 steps

1: aq. Na₂CO₃

2: HCl

3: CSA / tetrahydrofuran

4: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

5: aq. AcOH

6: pyridine / CH₂Cl₂

7: 75 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

8: NaOMe; MeOH

9: CSA / acetone

10: DMAP; pyridine / CH₂Cl₂

11: aq. AcOH

12: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

13: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

With pyridine; hydrogenchloride; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; barium dihydroxide; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; sodium carbonate; acetic acid; potassium bromide; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1: Acylation / 2: Glycosidation / 3: Acetalization / 4: Alkylation / 5: Hydrolysis / 6: Acetylation / 7: Glycosidation / 8: Deacetylation / 9: Acetalization / 10: Acetylation / 11: Hydrolysis / 12: Oxidation / 13: Oxidation;
DOI:10.1016/S0960-894X(99)00550-8