methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside
• CAS No.: 420121-00-2
• Molecular Formula: C₃₅H₄₇NO₁₀
• Molecular Weight: 641.759
• Mol file: 420121-00-2.mol

Synonyms:methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside

Chemical Property of methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside

There total 4 articles about methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside 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: 48.0%

(3aR,4S,6aS)-tert-butyl 4-formyl-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate (117781-13-2) + methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-3-deoxy-2-O-[(trifluoromethyl)sulfonyl]-α-D-erythro-hex-2-enopyranoside (420120-99-6) → methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside (420121-00-2)

Guidance literature:

With chromium dichloride; oxygen; nickel dichloride; In N,N-dimethyl-formamide; ultrasonication;

DOI:10.1002/1522-2675(200201)85:1<152::AID-HLCA152>3.0.CO;2-L

Reference yield:

(3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate (117956-54-4) → methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside (420121-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaHCO₃; Pb(OAc)4 / CH₂Cl₂ / 0.83 h / -78 °C

2: 48 percent / O₂; CrCl₂; NiCl₂ / dimethylformamide / ultrasonication

With chromium dichloride; lead(IV) acetate; oxygen; sodium hydrogencarbonate; nickel dichloride; In dichloromethane; N,N-dimethyl-formamide; 2: Nozaki-Kishi coupling;

DOI:10.1002/1522-2675(200201)85:1<152::AID-HLCA152>3.0.CO;2-L

Reference yield:

Trifluoro-methanesulfonic acid (1R,2S,5R)-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-en-4-yl ester (251085-95-7) → methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-3-deoxy-α-D-erythro-hex-2-enopyranoside (420121-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / BF₃*Et₂O / 20 °C

2: 68 percent / iPr₂NH / 20 °C

3: 48 percent / O₂; CrCl₂; NiCl₂ / dimethylformamide / ultrasonication

With chromium dichloride; boron trifluoride diethyl etherate; oxygen; diisopropylamine; nickel dichloride; In N,N-dimethyl-formamide; 3: Nozaki-Kishi coupling;

DOI:10.1002/1522-2675(200201)85:1<152::AID-HLCA152>3.0.CO;2-L

upstream raw materials:

(3aR,4S,6aS)-tert-butyl 4-formyl-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-3-deoxy-2-O-[(trifluoromethyl)sulfonyl]-α-D-erythro-hex-2-enopyranoside

(3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

Trifluoro-methanesulfonic acid (1R,2S,5R)-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-en-4-yl ester

Downstream raw materials:

methyl 4-O-benzyl-6-O-[(benzyloxy)methyl]-2-{(1S)-2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribitol-1-C-yl}-2-deoxy-α-D-glucopyranoside