(diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Base Information

• Chemical Name: (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
• CAS No.: 366805-09-6
• Molecular Formula: C₆₆H₉₅NO₁₀
• Molecular Weight: 1062.48

Synonyms:(diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Chemical Property of (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

There total 7 articles about (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-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:

Allyl 3-O-<(3R)-3-benzyloxytetradecanyl>-2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-D-glucopyranoside (132791-92-5) → (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside (366805-09-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOH / ethanol; H₂O / 5 h / 60 °C

1.2: 89 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

2.1: OsO₄; 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

3.1: Pb(OAc)4 / benzene / 1 h / 20 °C

4.1: NaH₂PO₄; NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

5.1: 2.57 g / ethyl acetate / 18 h / 20 °C

With lead(IV) acetate; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; 4-methylmorpholine N-oxide; In tetrahydrofuran; ethanol; water; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1016/S0008-6215(02)00357-9

Reference yield:

1-O-allyl-2-deoxy-4,6-isopropylidene-2-(trifluoroacetamido)-α-D-glucopyranoside (139629-59-7) → (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside (366805-09-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 74 percent / NaH / dimethylformamide / 6 h / 20 °C

2.1: NaOH / ethanol; H₂O / 5 h / 60 °C

2.2: 89 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

3.1: OsO₄; 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

4.1: Pb(OAc)4 / benzene / 1 h / 20 °C

5.1: NaH₂PO₄; NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

6.1: 2.57 g / ethyl acetate / 18 h / 20 °C

With lead(IV) acetate; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0008-6215(02)00357-9

Reference yield:

(R)-3-benzyloxy-1-(methanesulfonyloxy)tetradecane (137119-93-8) → (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside (366805-09-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 74 percent / NaH / dimethylformamide / 6 h / 20 °C

2.1: NaOH / ethanol; H₂O / 5 h / 60 °C

2.2: 89 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

3.1: OsO₄; 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

4.1: Pb(OAc)4 / benzene / 1 h / 20 °C

5.1: NaH₂PO₄; NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

6.1: 2.57 g / ethyl acetate / 18 h / 20 °C

With lead(IV) acetate; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0008-6215(02)00357-9

upstream raw materials:

diazodiphenylmethane

[(4aR,6S,7R,8R,8aS)-7-((R)-3-Benzyloxy-tetradecanoylamino)-8-((R)-3-benzyloxy-tetradecyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-acetic acid

(R)-3-benzyloxy-1-(methanesulfonyloxy)tetradecane

Allyl 3-O-<(3R)-3-benzyloxytetradecanyl>-2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-D-glucopyranoside

Downstream raw materials:

(diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-α-D-glucopyranoside

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