(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane

Base Information

• Chemical Name: (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane
• CAS No.: 429675-56-9
• Molecular Formula: C₃₀H₃₃IO₅
• Molecular Weight: 600.494

Synonyms:(2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane

Chemical Property of (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane

Chemical Property:

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Technology Process of (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane

There total 4 articles about (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane 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: 98.0%

1-(1,3,4,6-tetra-O-benzyl-α-D-fructofuranosyl)-2-propene (111085-79-1) → (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane (429675-56-9)

Guidance literature:

With iodine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)02393-0

Reference yield:

benzyl bromide (100-39-0) → (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane (429675-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NaH / dimethylformamide

2: 57 percent / boron trifluoride etherate

3: 98 percent / I₂ / tetrahydrofuran

With iodine; sodium hydride; boron trifluoride diethyl etherate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)02393-0

Reference yield:

methyl D-fructofuranoside (13403-14-0,15219-93-9,16975-88-5,51295-55-7,51295-56-8,52443-09-1,60504-77-0,60504-79-2,69460-17-9,92283-23-3,63526-47-6) → (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane (429675-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NaH / dimethylformamide

2: 57 percent / boron trifluoride etherate

3: 98 percent / I₂ / tetrahydrofuran

With iodine; sodium hydride; boron trifluoride diethyl etherate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)02393-0

upstream raw materials:

1-(1,3,4,6-tetra-O-benzyl-α-D-fructofuranosyl)-2-propene

benzyl bromide

methyl D-fructofuranoside

Downstream raw materials:

1-(3,4,6-tri-O-benzyl-α-D-fructofuranosyl)-2-propene

(2S,3R,3aS,5R,6R,6aS)-3a-Allyl-2-azidomethyl-6-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]furan-3-ol

(R)-1-((2S,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-prop-2-en-1-ol

(2R,3R,3aS,5R,6R,6aS)-3a-Allyl-6-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]furan-3-ol

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